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Named reactions

Get references and more from over 225 named organic chemical reaction

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Search synthesis

Michael Addition

Michael Addition

Mechanism of the Michael Addition

Reference

Original reference J. Prakt. Chem. 1887, 35, 349.
Wikipedia link
Organic chemistry portal link


Sample reactions

This reaction is from the synthesis of Quinine by Eric N. Jacobsen. Show me the full synthesis.

Reactant structure
Reagent structureMethyl Cyanoacetate
Reaction arrow head
Cyclohexane, t-BuOH
RT, 48 h
91 %
Product structure

This reaction is from the synthesis of Strychnine by Robert B. Woodward. Show me the full synthesis.

Reactant structure
NaSBn
Reaction arrow head
MeOH
RT, 3 h
77 %
Product structure

This reaction is from the synthesis of Strychnine by Robert B. Woodward. Show me the full synthesis.

Reactant structure
KOH
Reaction arrow head
EtOH
100 °C, 5 h
Product structure

This reaction is from the synthesis of Strychnine by Larry E. Overman. Show me the full synthesis.

Reactant structure
t-BuOOH, Me3N+Bn HO-
Reaction arrow head
THF
-15 °C
91 %
Product structure

This reaction is from the synthesis of Erythromycin A by Robert B. Woodward. Show me the full synthesis.

Reactant structure
BnSH, n-BuLi
Reaction arrow head
THF
-50 °C
85 % (4 steps)
Product structure

This reaction is from the synthesis of Erythromycin A by Pierre Deslongchamps. Show me the full synthesis.

Reactant structure
MeLi, CuBr, Bz2O2
Reaction arrow head
Et2O
-78 to 0 °C, 45 min
75 %
Product structure

This reaction is from the synthesis of Cephalosporin C1 by Robert B. Woodward. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
80 °C, 16 h
Product structure

This reaction is from the synthesis of Ginkgolide B by Elias J. Corey. Show me the full synthesis.

Reactant structure
t-BuLi, CuCN, TMSCl
Reaction arrow head
Et2O, Et3N
-78 to -10 °C, 3 h
93 %
Product structure

This reaction is from the synthesis of Ginkgolide B by Elias J. Corey. Show me the full synthesis.

Reactant structure
Ph3COOH, Et3NBn+ i-PrO-
Reaction arrow head
THF
-10 °C, 3 h
72 %
Product structure

This reaction is from the synthesis of Alkaloid 251F by Jeffrey Aubé. Show me the full synthesis.

Reactant structure + Reactant structure
MeLi, CuI
Reaction arrow head
THF
0 °C to RT, 45 min
60 %
Product structure

This reaction is from the synthesis of Penitrem D by Amos B. Smith, III. Show me the full synthesis.

Reactant structure
MeLi, CuI, TMSCl
Reaction arrow head
Et2O, Et3N
0 °C to RT, 3.5 h
80 %
Product structure

This reaction is from the synthesis of Penitrem D by Amos B. Smith, III. Show me the full synthesis.

Reactant structure
VinylMgBr, CuI, (CH2NMe2)2, TMSCl
Reaction arrow head
THF, Et3N
90 %
Product structure

This reaction is from the synthesis of Sarain A by Larry E. Overman. Show me the full synthesis.

Reactant structure + Reactant structure
TMS2NLi
Reaction arrow head
THF, DME
-78 °C, 4.5 h
71 %
Product structure

This reaction is from the synthesis of Tetrodotoxin by Justin Du Bois. Show me the full synthesis.

Reactant structure
VinylMgBr, CuI
Reaction arrow head
THF
Product structure

This reaction is from the synthesis of Aspidophytine by Elias J. Corey. Show me the full synthesis.

Reactant structure + Reactant structure
CeCl3
Reaction arrow head
THF
0 °C
82 %
Product structure

This reaction is from the synthesis of Cholesterol by Robert B. Woodward. Show me the full synthesis.

Reactant structure
Ethyl vinyl ketone, KOt-Bu, NaOH
Reaction arrow head
t-BuOH, H2O
0 °C to RT, 10 h
53 %
Product structure

This reaction is from the synthesis of Cholesterol by Robert B. Woodward. Show me the full synthesis.

Reactant structure
VinylCN, Me3N+Bn HO-
Reaction arrow head
PhH, t-BuOH, H2O
50 °C, 45 h
Product structure

This reaction is from the synthesis of Modhephene by Viresh H. Rawal. Show me the full synthesis.

Reactant structure
MeLi, CuCN, BF3.OEt2
Reaction arrow head
THF
Product structure

This reaction is from the synthesis of Indolizidine 223A by Dawei Ma. Show me the full synthesis.

Reactant structure + Reactant structure
n-BuLi
Reaction arrow head
THF
-78 °C to RT, 6 h
67 %
Product structure

This reaction is from the synthesis of Taxol by Paul A. Wender. Show me the full synthesis.

Reactant structure
MeLi, CuI
Reaction arrow head
Et2O
-78 °C to RT, ON
97 %
Product structure

This reaction is from the synthesis of Taxol by Isao Kuwajima. Show me the full synthesis.

Reactant structure
i-PrCO2Et, i-Pr2NLi
Reaction arrow head
THF
-78 to 0 °C, 2.5 h
Product structure

This reaction is from the synthesis of Taxol by Teruaki Mukaiyama. Show me the full synthesis.

Reactant structure + Reactant structure
t-BuLi, CuCN
Reaction arrow head
Et2O
-78 to 0 °C, 2 h
92 %
Product structure

This reaction is from the synthesis of Fredericamycin A by Dale L. Boger. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi
Reaction arrow head
THF
-78 °C to RT, 3 h
64-85 %
Product structure

This reaction is from the synthesis of Cortistatin A by Phil S. Baran. Show me the full synthesis.

Reactant structure
t-BuOOH, DBU
Reaction arrow head
THF
RT, 72 h
82 %
Product structure

This reaction is from the synthesis of Ingenol by John L. Wood. Show me the full synthesis.

Reactant structure
MeLi, CuCN
Reaction arrow head
Et2O
-78 °C, 2 h
Product structure

This reaction is from the synthesis of Ingenol by Jeffrey D. Winkler. Show me the full synthesis.

Reactant structure + Reactant structure
Li, NH3
Reaction arrow head
THF, t-BuOH
-78 to -5 °C, 75 min
Product structure

This reaction is from the synthesis of Cyanocobalamin by Robert B. Woodward. Show me the full synthesis.

Reactant structure
KOt-Bu
Reaction arrow head
t-BuOH
Product structure

This reaction is from the synthesis of Gymnomitrol by Robert M. Coates. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
PhH
Reflux, 22 h
76 %
Product structure

This reaction is from the synthesis of Gymnomitrol by Leo A. Paquette. Show me the full synthesis.

Reactant structure + Reactant structure
CuBr.Me2S, MeI
Reaction arrow head
HMPA
66 %
Product structure

This reaction is from the synthesis of Gymnomitrol by Steven C. Welch. Show me the full synthesis.

Reactant structure
Me2CuLi, AllylCl
Reaction arrow head
THF, HMPA
-78 °C to RT
Product structure

This reaction is from the synthesis of Murrayazoline by Noritaka Chida. Show me the full synthesis.

Reactant structure
Sc(OTf)3
Sealed tube
Reaction arrow head
DCE, H2O
120 °C, 36 h
73 %
Product structure

This reaction is from the synthesis of Morphine by James D. White. Show me the full synthesis.

Reactant structure + Reactant structure
Et3N
Reaction arrow head
CH2Cl2
RT, 12 h
Product structure

This reaction is from the synthesis of Epolactaene by Yujiro Hayashi. Show me the full synthesis.

Reactant structure
Ph3COOH, n-BuLi
Reaction arrow head
THF
-78 °C, 2 h
Product structure

This reaction is from the synthesis of Morphine by Catherine Guillou. Show me the full synthesis.

Reactant structure
BnNHMe
Reaction arrow head
RT, 16 h
Product structure

This reaction is from the synthesis of Morphine by Johann Mulzer. Show me the full synthesis.

Reactant structure
Vinyl2CuMgCl, TMSCl, Et3N
Reaction arrow head
THF
-78 °C to RT
Product structure

This reaction is from the synthesis of Mersicarpine by Michael A. Kerr. Show me the full synthesis.

Reactant structure + Reactant structure
K2CO3
Reaction arrow head
THF
Reflux, 4 h
98 %
Product structure

This reaction is from the synthesis of Mersicarpine by Michael A. Kerr. Show me the full synthesis.

Reactant structure
VinylCN, KOt-Bu
Reaction arrow head
THF
0 °C, 20 min
74 %
Product structure

This reaction is from the synthesis of Kinamycin F by Seth B. Herzon. Show me the full synthesis.

Reactant structure
TMSCH2MgCl, CuI, TMSCl, Et3N
Reaction arrow head
THF, HMPA
-78 °C to RT, 2 h
Product structure

This reaction is from the synthesis of Kinamycin F by Seth B. Herzon. Show me the full synthesis.

Reactant structure + Reactant structure
TASF
Reaction arrow head
CH2Cl2
-78 °C, 5 min
79 %
Product structure

This reaction is from the synthesis of Kinamycin F by Kyriacos C. Nicolaou. Show me the full synthesis.

Reactant structure
MeMgBr, CuBr.Me2S, TMSCl
Reaction arrow head
THF, HMPA
-78 °C to RT, 2.5 h
Product structure

This reaction is from the synthesis of Laurenene by Michael T. Crimmins. Show me the full synthesis.

Reactant structure + Reactant structure + Reactant structure
(n-Bu3PCuI)4, HMPA
Reaction arrow head
THF
-50 °C to RT, 3 h
60 %
Product structure

This reaction is from the synthesis of Laurenene by Michael T. Crimmins. Show me the full synthesis.

Reactant structure
Me2CuLi
Reaction arrow head
Et2O
-78 °C, 30 min
Product structure

This reaction is from the synthesis of Laurenene by Michael T. Crimmins. Show me the full synthesis.

Reactant structure
Me2CuLi
Reaction arrow head
Et2O
-78 °C, 30 min
Product structure

This reaction is from the synthesis of Laurenene by Leo A. Paquette. Show me the full synthesis.

Reactant structure + Reactant structure
CuBr.Me2S
Reaction arrow head
THF, Me2S
-78 to 0 °C, 6 h
Product structure

This reaction is from the synthesis of Laurenene by Leo A. Paquette. Show me the full synthesis.

Reactant structure + Reactant structure
CuBr.Me2S
Reaction arrow head
THF, Me2S
-78 to 0 °C
68 %
Product structure

This reaction is from the synthesis of Longifolene by Elias J. Corey. Show me the full synthesis.

Reactant structure
Et3N
Sealed tube
Reaction arrow head
Ethylene Glycol
225 °C, 24 h
8-12 %
Product structure

This reaction is from the synthesis of Longifolene by John E. McMurry. Show me the full synthesis.

Reactant structure
Me2CuLi
Reaction arrow head
Et2O
-20 °C, 40 min
96 %
Product structure

This reaction is from the synthesis of Longifolene by William S. Johnson. Show me the full synthesis.

Reactant structure + Reactant structure
t-BuLi, (n-Bu3PCuI)4, AcCl
Reaction arrow head
Et2O
-78 to 0 °C
84 %
Product structure

This reaction is from the synthesis of Quadrone by Samuel J. Danishefsky. Show me the full synthesis.

Reactant structure + Reactant structure
VinylMgBr, (n-Bu3PCuI)4
Reaction arrow head
THF, HMPA
-45 °C to RT, 3 h
54 %
Product structure

This reaction is from the synthesis of Quadrone by Samuel J. Danishefsky. Show me the full synthesis.

Reactant structure + Reactant structure
TiCl4
Reaction arrow head
CH2Cl2
-78 °C to RT, 40 min
Product structure

This reaction is from the synthesis of Quadrone by Steven D. Burke. Show me the full synthesis.

Reactant structure
Morpholine, TsOH
Reaction arrow head
PhH
Reflux
92 %
Product structure

This reaction is from the synthesis of Quadrone by Steven D. Burke. Show me the full synthesis.

Reactant structure
t-BuOOH, NaOH
Reaction arrow head
MeOH, H2O
RT
89 % (2 steps)
Product structure

This reaction is from the synthesis of Nominine by David Y. Gin. Show me the full synthesis.

Reactant structure
Et2AlCN, n-Bu4N+ Ph3SiF2-, Tf2O
Reaction arrow head
PhH
0 °C to RT, 19.5 h
81 %
Product structure

This reaction is from the synthesis of Pactamycin by Stephen Hanessian. Show me the full synthesis.

Reactant structure
H2O2, NaOH
Reaction arrow head
CH2Cl2, MeOH, H2O
0 °C, 2 h
75 %
Product structure

This reaction is from the synthesis of Cylindrospermopsin by Barry B. Snider. Show me the full synthesis.

Reactant structure
VinylMgBr, CuBr.Me2S, TMSCl
Reaction arrow head
THF
-78 °C, 2 h
92 %
Product structure

This reaction is from the synthesis of Retigeranic Acid by Leo A. Paquette. Show me the full synthesis.

Reactant structure + Reactant structure
CuBr.Me2S
Reaction arrow head
THF, Me2S
-78 to 0 °C, 24 h
Product structure

This reaction is from the synthesis of Retigeranic Acid by Leo A. Paquette. Show me the full synthesis.

Reactant structure
VinylMgBr, CuBr.Me2S
Reaction arrow head
50 %
Product structure

This reaction is from the synthesis of Retigeranic Acid by Leo A. Paquette. Show me the full synthesis.

Reactant structure + Reactant structure
Mg
Reaction arrow head
Et2O
Reflux
13 %
Product structure

This reaction is from the synthesis of Retigeranic Acid by Tomas Hudlicky. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi
Reaction arrow head
THF
-100 to -78 °C
50 %
Product structure

This reaction is from the synthesis of Morphine by Marshall D. Gates. Show me the full synthesis.

Reactant structure
NCCH2CO2Et, K3Fe(CN)6, Et3N
Reaction arrow head
EtOH, H2O
RT, 11 min
84 %
Product structure

This reaction is from the synthesis of Mesembrine by Maurice Shamma. Show me the full synthesis.

Reactant structure
NaOCl
Reaction arrow head
Pyr, H2O
0 °C, 60 min
90 %
Product structure

This reaction is from the synthesis of Mesembrine by Maurice Shamma. Show me the full synthesis.

Reactant structure
HCl
Reaction arrow head
EtOH, H2O
Reflux, 4 h
50 % (2 steps)
Product structure

This reaction is from the synthesis of Oseltamivir by Yujiro Hayashi. Show me the full synthesis.

Reactant structure + Reactant structure + Reactant structure
Reagent structureClCH2CO2H
Reaction arrow head
CH2Cl2
0 °C to RT, 3.5 h
Product structure

This reaction is from the synthesis of Oseltamivir by Yujiro Hayashi. Show me the full synthesis.

Reactant structure
p-MePhSH
Reaction arrow head
EtOH
-15 °C, 36 h
70 % (2 steps)
Product structure

This reaction is from the synthesis of Morphine by Gilbert Stork. Show me the full synthesis.

Reactant structure
Methyl propynoate, Et3N
Reaction arrow head
THF
-20 to 0 °C, 3.5 h
89 %
Product structure

This reaction is from the synthesis of Strychnine by Christopher D. Vanderwal. Show me the full synthesis.

Reactant structure
TMS2NNa, CuBr.Me2S
Reaction arrow head
NMP
0 to 65 °C, 95 min
10 %
Product structure

This reaction is from the synthesis of Strychnine by Philip Magnus. Show me the full synthesis.

Reactant structure
NaH
Reaction arrow head
THF
0 °C, 105 min
98 %
Product structure

This reaction is from the synthesis of Strychnine by Masakatsu Shibasaki. Show me the full synthesis.

Reactant structure
Reagent structureDimethyl malonate, KOt-Bu
4Å MS
Reaction arrow head
THF
4 °C to RT, 24 h
91 %
Product structure

This reaction is from the synthesis of Strychnine by Masakatsu Shibasaki. Show me the full synthesis.

Reactant structure + Reactant structure
Tf2O, i-Pr2NEt
Reaction arrow head
CH2Cl2
-78 °C, 90 min
Product structure

This reaction is from the synthesis of Strychnine by David W. C. MacMillan. Show me the full synthesis.

Reactant structure + Reactant structure
Reagent structureBr3CCO2H
Reaction arrow head
PhMe
-60 °C to RT, 23 h
82 %
Product structure

This reaction is from the synthesis of Hirsutene by Steven V. Ley. Show me the full synthesis.

Reactant structure + Reactant structure
Mg, CuBr.Me2S
Reaction arrow head
THF
-50 °C to RT, 80 min
58 %
Product structure

This reaction is from the synthesis of Hirsutene by Raymond L. Funk. Show me the full synthesis.

Reactant structure + Reactant structure
TiCl4
Reaction arrow head
CH2Cl2
71 %
Product structure

This reaction is from the synthesis of Azadirachtin by Steven V. Ley. Show me the full synthesis.

Reactant structure
TMS2NLi
Reaction arrow head
THF
0 °C to RT, 100 min
100 %
Product structure

This reaction is from the synthesis of Hirsutene by Philip Magnus. Show me the full synthesis.

Reactant structure + Reactant structure
t-BuLi, CuI, BF3.OEt2
Reaction arrow head
Et2O, HMPT
-120 to -20 °C, 9 h
60 %
Product structure

This reaction is from the synthesis of Hirsutene by Duy H. Hua. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi, AcCl
Reaction arrow head
THF, HMPA
-78 °C, 105 min
86 %
Product structure

This reaction is from the synthesis of Hirsutene by Duy H. Hua. Show me the full synthesis.

Reactant structure + Reactant structure
Li, CuI.Me2S
Reaction arrow head
Et2O
-30 °C to RT, 2.5 h
85 %
Product structure

This reaction is from the synthesis of Centrohexaindane by Dietmar Kuck. Show me the full synthesis.

Reactant structure + Reactant structure
Reaction arrow head
AcOH
100 °C, 60 min
63 %
Product structure

This reaction is from the synthesis of Hirsutene by Michel Franck-Neumann. Show me the full synthesis.

Reactant structure + Reactant structure
CuBr.Me2S
Reaction arrow head
THF
-78 °C, 15 h
Product structure

This reaction is from the synthesis of Streptonigrone by Marco A. Ciufolini. Show me the full synthesis.

Reactant structure + Reactant structure
KOt-Bu
Reaction arrow head
DMSO
RT to 100 °C, 10 h
60 %
Product structure

This reaction is from the synthesis of Coccinelline by Robert V. Stevens. Show me the full synthesis.

Reactant structure + Reactant structure
NaOMe
Reaction arrow head
MeOH
RT, 12 h
58 %
Product structure

This reaction is from the synthesis of Trifarienol B by Toshio Honda. Show me the full synthesis.

Reactant structure
MeLi, CuI
Reaction arrow head
-78 to -40 °C, 80 min
93 %
Product structure

This reaction is from the synthesis of Trifarienol B by Toshio Honda. Show me the full synthesis.

Reactant structure
Reagent structureVinylMgBr
Reaction arrow head
THF
-78 to 0 °C, 12.5 h
90 %
Product structure

This reaction is from the synthesis of Capnellene by Leo A. Paquette. Show me the full synthesis.

Reactant structure
MeLi.LiBr, CuI
Reaction arrow head
Et2O
0 °C, 30 min
80 %
Product structure

This reaction is from the synthesis of Capnellene by Leo A. Paquette. Show me the full synthesis.

Reactant structure
VinylMgBr, CuI
Reaction arrow head
THF
-78 °C to RT, 30 min
55 %
Product structure

This reaction is from the synthesis of Echitamidine by Joan Bosch. Show me the full synthesis.

Reactant structure
Methyl vinyl ketone, Et3N
Reaction arrow head
MeOH
RT, 105 min
74 %
Product structure

This reaction is from the synthesis of Echitamidine by Joan Bosch. Show me the full synthesis.

Reactant structure
Me3N+Bn HO-
Reaction arrow head
DME
-20 °C, 2.5 h
44 %
Product structure

This reaction is from the synthesis of Marinopyrrole B by Derrick L. J. Clive. Show me the full synthesis.

Reactant structure + Reactant structure
K2CO3
Reaction arrow head
MeCN
Reflux, 42 h
95 %
Product structure
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