Enantioselective synthesis of α-hydroxy acids employing (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide as chiral auxiliary

被引：47
作者：
Chang, JW
Jang, DP
Uang, BJ [1 ]
Liao, FL
Wang, SL
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
[2] Natl Tsing Hua Univ, Instrumentat Ctr, Hsinchu 300, Taiwan
来源：
ORGANIC LETTERS | 1999年 / 1卷 / 13期
关键词：
D O I：
10.1021/ol9910666
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with alpha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantiomeric excesses.
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页码：2061 / 2063
页数：3
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