Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral α-amino acids

被引:33
作者
Bull, SD [1 ]
Davies, SG [1 ]
Garner, AC [1 ]
O'Shea, MD [1 ]
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 24期
关键词
D O I
10.1039/b108621a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of a range of organocuprates to (S)-N,N'-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2,5-dione 8 affords cis-3-isopropyl-6-alkyldiketopiperazines in excellent yield and >95% de. Subsequent deprotection and hydrolysis of these cis-3-isopropyl-6-alkyldiketopiperazines affords homochiral (S)-alpha -amino acids in excellent yield.
引用
收藏
页码:3281 / 3287
页数:7
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