Asymmetric synthesis of α,α-disubstituted α-amino acids using (S,S)-cyclohexane-1,2-diol as a chiral auxiliary

被引：46

作者：

Tanaka, M ^{[1
]}

Oba, M ^{[1
]}

Tamai, K ^{[1
]}

Suemune, H ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 08期

关键词：

D O I：

10.1021/jo001423m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective alkylation of ethyl 2-methyl- and/or 2-ethylacetoacetates using the (S,S)cyclohexane-1,2-diol as an acetal chiral auxiliary afforded enol ethers (2a-f and 5a-f) of 92 - > 95% de in 31-70% yields. Removal of the cyclohexane-l,2-diol with BF3-OEt2 afforded beta -keto esters (3 and 6) bearing a chiral quaternary carbon. The beta -keto esters could be easily converted into optically active alpha -methylated and/or alpha -ethylated alpha,alpha -disubstituted amino acids (12 and 13) in 21-99% yields using Schmidt rearrangement.

引用

页码：2667 / 2673

页数：7

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