ChemInform Abstract: In situ Formed Bifunctional Primary Amine-Imine Catalyst: Application to the Construction of Chiral Tertiary Alcohols Through Asymmetric Aldol-Type Reaction.

ChemInform ◽  
2013 ◽  
Vol 44 (50) ◽  
pp. no-no
Author(s):  
Zhijie Mao ◽  
Xi Zhu ◽  
Aijun Lin ◽  
Weipeng Li ◽  
Yan Shi ◽  
...  
Keyword(s):  
Primary Amine ◽  
Asymmetric Aldol ◽  
Type Reaction ◽  
Tertiary Alcohols ◽  
Chiral Tertiary Alcohols

scholarly journals Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3902
Author(s):  
Mei Kee Kam ◽  
Akira Sugiyama ◽  
Ryouta Kawanishi ◽  
Kazutaka Shibatomi
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Substitution ◽  
Primary Amine ◽  
Tetrabutylammonium Hydroxide ◽  
Tertiary Alcohols ◽  
Tertiary Carbon ◽  
Chiral Tertiary Alcohols

Chiral tertiary α-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium hydroxide yielded the corresponding α-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. The proposed method would be useful for the preparation of chiral tertiary alcohols.

In Situ Formed Bifunctional Primary Amine-Imine Catalyst for Asymmetric Aldol Reactions of α-Keto Esters

2011 ◽  
Vol 17 (30) ◽  
pp. 8281-8284 ◽  
Author(s):  
Xi Zhu ◽  
Aijun Lin ◽  
Ling Fang ◽  
Wei Li ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Primary Amine ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Keto Esters

Asymmetric Synthesis of Chiral Tertiary Alcohols in High Enantiomeric Excess

1982 ◽  
pp. 37-53 ◽  
Author(s):  
ERNEST L. ELIEL ◽  
JORMA K. KOSKIMIES ◽  
BRUNO LOHRI ◽  
W. JACK FRAZEE ◽  
SUSAN MORRIS-NATSCHKE ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomeric Excess ◽  
Tertiary Alcohols ◽  
Chiral Tertiary Alcohols
Sign in / Sign up

Export Citation Format

Share Document