Stereoselective synthesis of a set of two functionalized (E)-alkene dipeptide isosteres of L-amino acid-L-Glu and L-amino acid-D-Glu

被引：26
作者：
Oishi, S
Tamamura, H [1 ]
Yamashita, M
Odagaki, Y
Hamanaka, N
Otaka, A
Fujii, N
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
[2] Ono Pharmaceut Co Ltd, Minase Res Inst, Osaka 6188585, Japan
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 19期
关键词：
D O I：
10.1039/b103833h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of N-arylsulfonyl-gamma,delta -cis- or -trans-gamma,delta -epimino (E)-alpha,beta -enoates with HCl-1,4-dioxane affords regio- and stereo-selective ring-opened products, delta -aminated gamma -chloro-alpha,beta -enoates. This ring-opening reaction provides a useful method for the stereoselective synthesis of a set of diastereomeric (L-Xaa, L-Glu)-type and (L-Xaa, D-Glu)-type (E)-alkene dipeptide isosteres (EADIs) from a single substrate of gamma,delta -epimino (E)-alpha,beta -enoate using organozinc-copper reagents.
引用
收藏
页码：2445 / 2451
页数：7
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