Asymmetric Synthesis of Functionalized Tertiary Alcohols by Diastereoselective Aldol Reaction of Silyl Enol Ether and Ketene Silyl Acetal with α-Keto Esters Bearing an Optically Active Cyclitol as a Chiral Auxiliary

Synlett ◽  
1994 ◽  
Vol 1994 (04) ◽  
pp. 275-276 ◽  
Author(s):  
Takahiko AKIYAMA ◽  
Keiichiro ISHIKAWA ◽  
Shoichiro OZAKI
Keyword(s):  
Asymmetric Synthesis ◽  
Aldol Reaction ◽  
Optically Active ◽  
Chiral Auxiliary ◽  
Enol Ether ◽  
Tertiary Alcohols ◽  
Keto Esters ◽  
Silyl Enol Ether

An improved synthesis of sitophilure

2009 ◽  
Vol 87 (1) ◽  
pp. 30-32 ◽  
Author(s):  
Cuifen Lu ◽  
Junqi Nie ◽  
Guichun Yang ◽  
Zuxing Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Aldol Reaction ◽  
Enantiomeric Excess ◽  
Chiral Auxiliary

The asymmetric synthesis of sitophilure was carried out in 8 steps, with 42% overall yield and 97% enantiomeric excess from propionaldehyde. The synthesis relied on an approach employing an asymmetric acyl-thiazolidinethione propionate aldol reaction to establish two stereogenic centers.Key words: sitophilure, thiazolidinethione, chiral auxiliary, synthesis.

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