Enantioselective intramolecular C-H insertion route to a key intermediate for the synthesis of trinem antibiotics

被引：41

作者：

Anada, M ^{[1
]}

Hashimoto, S ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期

关键词：

antibiotics; insertion reactions; rhodium and compounds; enantioselection;

D O I：

10.1016/S0040-4039(98)02055-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to the enantiomerically pure azetidin-2-one 3, a key intermediate for the synthesis of trinems, has been developed, incorporating enantioselective intramolecular C-H insertion of alpha-methoxycarbonyl-alpha-diazoacetamide catalyzed by chiral Rh(II) complexes and diastereoselective arene hydrogenation as the key steps. The use of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] as a catalyst produced the desired azetidinone in 84% ee, whereas catalysis with dirhodium(II) tetrakis[N-phthaloyl-(S)-alaninate] afforded its enantiomer in 84%ee. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9063 / 9066

页数：4

共 26 条

[1] Enantioselective synthesis of 4-substituted 2-pyrrolidinones by site-selective C-H insertion of α-methoxycarbonyl-α-diazoacetanilides catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] [J].