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

Methyl Cyanoacetate

Cyclohexane, t-BuOH
RT, 48 h
91 %

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

NaSBn

MeOH
RT, 3 h
77 %

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

KOH

EtOH
100 °C, 5 h

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

t-BuOOH, Me₃N⁺Bn HO^-

THF
-15 °C
91 %

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

BnSH, n-BuLi

THF
-50 °C
85 % (4 steps)

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

MeLi, CuBr, Bz₂O₂

Et₂O
-78 to 0 °C, 45 min
75 %

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

80 °C, 16 h

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

t-BuLi, CuCN, TMSCl

Et₂O, Et₃N
-78 to -10 °C, 3 h
93 %

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

Ph₃COOH, Et₃NBn⁺ i^-PrO^-

THF
-10 °C, 3 h
72 %

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

MeLi, CuI

THF
0 °C to RT, 45 min
60 %

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

MeLi, CuI, TMSCl

Et₂O, Et₃N
0 °C to RT, 3.5 h
80 %

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

VinylMgBr, CuI, (CH₂NMe₂)₂, TMSCl

THF, Et₃N
90 %

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

TMS₂NLi

THF, DME
-78 °C, 4.5 h
71 %

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

VinylMgBr, CuI

THF

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

CeCl₃

THF
0 °C
82 %

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

Ethyl vinyl ketone, KOt-Bu, NaOH

t-BuOH, H₂O
0 °C to RT, 10 h
53 %

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

VinylCN, Me₃N⁺Bn HO^-

PhH, t-BuOH, H₂O
50 °C, 45 h

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

MeLi, CuCN, BF₃^.OEt₂

THF

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

n-BuLi

THF
-78 °C to RT, 6 h
67 %

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

MeLi, CuI

Et₂O
-78 °C to RT, ON
97 %

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

i-Pr₂NLi, i-PrCO₂Et

THF
-78 to 0 °C, 2.5 h

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

t-BuLi, CuCN

Et₂O
-78 to 0 °C, 2 h
92 %

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

i-Pr₂NLi

THF
-78 °C to RT, 3 h
64-85 %

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

t-BuOOH, DBU

THF
RT, 72 h
82 %

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

MeLi, CuCN

Et₂O
-78 °C, 2 h

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

Li, NH₃

THF, t-BuOH
-78 to -5 °C, 75 min

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

KOt-Bu

t-BuOH

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

PhH
Reflux, 22 h
76 %

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

CuBr^.Me₂S, MeI

HMPA
66 %

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

Me₂CuLi, AllylCl

THF, HMPA
-78 °C to RT

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

Sc(OTf)₃
Sealed tube

DCE, H₂O
120 °C, 36 h
73 %

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

Et₃N

CH₂Cl₂
RT, 12 h

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

Ph₃COOH, n-BuLi

THF
-78 °C, 2 h

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

BnNHMe

RT, 16 h

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

Vinyl₂CuMgCl, TMSCl, Et₃N

THF
-78 °C to RT

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

K₂CO₃

THF
Reflux, 4 h
98 %

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

VinylCN, KOt-Bu

THF
0 °C, 20 min
74 %

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

TMSCH₂MgCl, CuI, TMSCl, Et₃N

THF, HMPA
-78 °C to RT, 2 h

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

TASF

CH₂Cl₂
-78 °C, 5 min
79 %

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

MeMgBr, CuBr^.Me₂S, TMSCl

THF, HMPA
-78 °C to RT, 2.5 h

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

(n-Bu₃PCuI)₄, HMPA

THF
-50 °C to RT, 3 h
60 %

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

Me₂CuLi

Et₂O
-78 °C, 30 min

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

Me₂CuLi

Et₂O
-78 °C, 30 min

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

CuBr^.Me₂S

THF, Me₂S
-78 to 0 °C, 6 h

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

CuBr^.Me₂S

THF, Me₂S
-78 to 0 °C
68 %

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

Et₃N
Sealed tube

Ethylene Glycol
225 °C, 24 h
8-12 %

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

Me₂CuLi

Et₂O
-20 °C, 40 min
96 %

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

t-BuLi, (n-Bu₃PCuI)₄, AcCl

Et₂O
-78 to 0 °C
84 %

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

VinylMgBr, (n-Bu₃PCuI)₄

THF, HMPA
-45 °C to RT, 3 h
54 %

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

TiCl₄

CH₂Cl₂
-78 °C to RT, 40 min

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

Morpholine, TsOH

PhH
Reflux
92 %

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

t-BuOOH, NaOH

MeOH, H₂O
RT
89 % (2 steps)

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

Et₂AlCN, n-Bu₄N⁺ Ph₃SiF₂^-, Tf₂O

PhH
0 °C to RT, 19.5 h
81 %

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

H₂O₂, NaOH

CH₂Cl₂, MeOH, H₂O
0 °C, 2 h
75 %

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

VinylMgBr, CuBr^.Me₂S, TMSCl

THF
-78 °C, 2 h
92 %

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

CuBr^.Me₂S

THF, Me₂S
-78 to 0 °C, 24 h

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

VinylMgBr, CuBr^.Me₂S

50 %

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

Et₂O
Reflux
13 %

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

i-Pr₂NLi

THF
-100 to -78 °C
50 %

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

NCCH₂CO₂Et, K₃Fe(CN)₆, Et₃N

EtOH, H₂O
RT, 11 min
84 %

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

NaOCl

Pyr, H₂O
0 °C, 60 min
90 %

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

HCl

EtOH, H₂O
Reflux, 4 h
50 % (2 steps)

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

ClCH₂CO₂H

CH₂Cl₂
0 °C to RT, 3.5 h

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

p-MePhSH

EtOH
-15 °C, 36 h
70 % (2 steps)

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

Methyl propynoate, Et₃N

THF
-20 to 0 °C, 3.5 h
89 %

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

TMS₂NNa, CuBr^.Me₂S

NMP
0 to 65 °C, 95 min
10 %

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

NaH

THF
0 °C, 105 min
98 %

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

Dimethyl malonate, KOt-Bu
4Å MS

THF
4 °C to RT, 24 h
91 %

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

Tf₂O, i-Pr₂NEt

CH₂Cl₂
-78 °C, 90 min

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

Br₃CCO₂H

PhMe
-60 °C to RT, 23 h
82 %

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

Mg, CuBr^.Me₂S

THF
-50 °C to RT, 80 min
58 %

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

TiCl₄

CH₂Cl₂
71 %

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

TMS₂NLi

THF
0 °C to RT, 100 min
100 %

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

t-BuLi, CuI, BF₃^.OEt₂

Et₂O, HMPT
-120 to -20 °C, 9 h
60 %

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

i-Pr₂NLi, AcCl

THF, HMPA
-78 °C, 105 min
86 %

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

Li, CuI^.Me₂S

Et₂O
-30 °C to RT, 2.5 h
85 %

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

AcOH
100 °C, 60 min
63 %

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

CuBr^.Me₂S

THF
-78 °C, 15 h

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

KOt-Bu

DMSO
RT to 100 °C, 10 h
60 %

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

NaOMe

MeOH
RT, 12 h
58 %