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Named reactions

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Aldol Addition

Aldol Addition

Mechanism of the Aldol Addition

Reference

Original reference Bull. Soc. Chim. Fr. 1872, 17, 436.
http://gallica.bnf.fr/ark:/12148/bpt6k281966q.image.r=Bulletin+de+la+Société+chimique+de+France.f447.langFR
Wikipedia link
Organic chemistry portal link


Sample reactions

This reaction is from the synthesis of Colchicine by David A. Evans. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi, (CO2H)2
Reaction arrow head
THF, THF
-70 °C, 2 h
Product structure

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

Reactant structure
NaOH
Reaction arrow head
THF, H2O
RT
Product structure

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

Reactant structure
NaOH
Reaction arrow head
THF
RT
Product structure

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

Reactant structure
O3, TsOH, Me2S
Reaction arrow head
EtOAc
90%
Product structure

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

Reactant structure
D-Proline
Reaction arrow head
MeCN
RT
Product structure

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

Reactant structure + Reactant structure
MesLi
Reaction arrow head
THF
-50 °C
Product structure

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

Reactant structure
EtCOSt-Bu, i-Pr2NLi
Reaction arrow head
THF
-110 °C
85%
Product structure

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

Reactant structure
EtCO2Me, Cp2ZrCl2, i-Pr2NLi
Reaction arrow head
THF
-78 °C to RT, 2 h
60%
Product structure

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

Reactant structure
EtCO2t-Bu, i-Pr2NLi
Reaction arrow head
THF, HMPA
-78 to -30 °C, 12 h
60%
Product structure

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

Reactant structure + Reactant structure
MeLi, MgBr2.OEt2
Reaction arrow head
Et2O
-5 °C to RT, 70 min
65%
Product structure

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

Reactant structure + Reactant structure
NaOAc
Reaction arrow head
THF
Product structure

This reaction is from the synthesis of Taxol by Robert A. Holton. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NMgBr
Reaction arrow head
THF
-23 °C to RT, 2.5 h
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 Paul A. Wender. Show me the full synthesis.

Reactant structure
ClCO2CH2CCl3, DMAP
Reaction arrow head
CH2Cl2
RT, 42 h
62%
Product structure

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

Reactant structure
i-PrCO2Me, i-Pr2NLi
Reaction arrow head
Et2O
-78 °C
65%
Product structure

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

Reactant structure
NaOMe
Reaction arrow head
MeOH, THF
0 °C
90%
Product structure

This reaction is from the synthesis of Elailoide by David A. Evans. Show me the full synthesis.

Reactant structure + Reactant structure
PhBCl2, i-Pr2NEt
Reaction arrow head
CH2Cl2
-78 to 0 °C, 2.5 h
66%
Product structure

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

Reactant structure
(CF3CO)2O, DMSO, DBU
Reaction arrow head
CH2Cl2
-78 °C to RT, 21 h
Product structure

This reaction is from the synthesis of Cortistatin A by Matthew D. Shair. Show me the full synthesis.

Reactant structure
NaOMe
Reaction arrow head
MeOH
70 °C, 2 h
49% (2 steps)
Product structure

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

Reactant structure
TMS2NLi, ZnBr2, MeCHO
Reaction arrow head
THF, Et2O
-78 to 0 °C, 2 h
71%
Product structure

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

Reactant structure
MeCO2t-Bu, i-Pr2NLi, LiBr
Reaction arrow head
Et2O
-78 °C, 90 min
91%
Product structure

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

Reactant structure
KOH
Reaction arrow head
MeOH
2.5 d
26%
Product structure

This reaction is from the synthesis of Grandisine D by Osamu Tamura. Show me the full synthesis.

Reactant structure + Reactant structure
n-Bu2BOTf, i-Pr2NEt
Reaction arrow head
CH2Cl2
-78 °C to RT, 2 h
100%
Product structure

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

Reactant structure
i-Pr2NLi, MeCHO
Reaction arrow head
THF, HMPA
-78 °C, 4.5 h
96%
Product structure

This reaction is from the synthesis of Stigmatellin A by Dieter Enders. Show me the full synthesis.

Reactant structure + Reactant structure
TiCl4, i-Pr2NEt
Reaction arrow head
CH2Cl2
-78 °C to RT, 3.5 h
64%
Product structure

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

Reactant structure
HCl
Reaction arrow head
Acetone, H2O
RT, 3 d
79% (2 steps)
Product structure

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

Reactant structure
HCl
Reaction arrow head
THF, H2O
RT
71%
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 Alex G. Fallis. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi, CdCl2
Reaction arrow head
THF
-40 to 0 °C, 2.5 h
73%
Product structure

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

Reactant structure
HCl
Reaction arrow head
Acetone, H2O
RT, 60 min
Product structure

This reaction is from the synthesis of Triquinacene by James M. Cook. Show me the full synthesis.

Reactant structure
HCl
Reaction arrow head
THF, H2O
RT, 7 d
86%
Product structure

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

Reactant structure
i-Pr2NLi, CH2O
Reaction arrow head
THF
-23 °C, 80 min
60%
Product structure

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

Reactant structure + Reactant structure
TMS2NLi
Reaction arrow head
THF
-78 °C, 55 min
Product structure

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

Reactant structure
TiCl4, i-Pr2NEt, TMSCl
Reaction arrow head
CH2Cl2
0 °C, 20 min
85%
Product structure

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

Reactant structure
HCl
Reaction arrow head
Acetone, H2O
RT, 3 d
72% (2 steps)
Product structure

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

Reactant structure + Reactant structure
i-Pr2NLi
Reaction arrow head
THF
-78 to 50 °C, 5 h
Product structure

This reaction is from the synthesis of Asteltoxin by Stuart L. Schreiber. Show me the full synthesis.

Reactant structure + Reactant structure
i-Pr2NLi, HMPA
Reaction arrow head
THF
-78 °C, 20 min
80%
Product structure

This reaction is from the synthesis of Strychnine by Rodrigo B. Andrade. Show me the full synthesis.

Reactant structure
Malonic Acid, NaOAc
Reaction arrow head
AcOH, Ac2O
110 °C, 2 h
49% (2 steps)
Product structure

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

Reactant structure
Malonic Acid, NaOAc
Reaction arrow head
AcOH, Ac2O
110 °C, 2 h
49% (2 steps)
Product structure

This reaction is from the synthesis of Strychnine by Tohru Fukuyama. Show me the full synthesis.

Reactant structure
Malonic Acid, NaOAc
Reaction arrow head
AcOH, Ac2O
110 °C, 2 h
42% (4 steps)
Product structure

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

Reactant structure
Malonic Acid, NaOAc
Reaction arrow head
AcOH, Ac2O
110 °C, 2 h
42% (2 steps)
Product structure

This reaction is from the synthesis of Strychnine by Martin E. Kuehne. Show me the full synthesis.

Reactant structure
Malonic Acid, NaOAc
Reaction arrow head
AcOH, Ac2O
110 °C
65%
Product structure

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

Reactant structure
Malonic Acid, NaOAc
Reaction arrow head
AcOH, Ac2O
120 °C, 2 h
69%
Product structure

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

Reactant structure
HCl
Reaction arrow head
THF, H2O
40 °C, 24 h
84% (2 steps)
Product structure

This reaction is from the synthesis of Corannulene by Jay S. Siegel. Show me the full synthesis.

Reactant structure + Reactant structure
KOH
Reaction arrow head
MeOH
RT, 30 min
85%
Product structure
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