Regioselective ring cleavage of chiral β-trichloromethyl-β-propiolactone with organoaluminum compounds for the synthesis of optically active intermediates

被引：17

作者：

Fujisawa, T ^{[1
]}

Ito, T ^{[1
]}

Nishiura, S ^{[1
]}

Shimizu, M ^{[1
]}

机构：

[1] Mie Univ, Dept Chem Mat, Tsu, Mie 5148507, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 52期

关键词：

lactones; asymmetric cleavage reaction; aluminum reagents; pheromone & drugs;

D O I：

10.1016/S0040-4039(98)02238-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel alkylating ring cleavage reaction of enantiomerically pure beta-trichloromethyl-beta-propiolactone as a chiral building block with organoaluminum compounds provided ring-opened products with a chiral trichloromethyl carbinol moiety. A product was demonstrated to be used as an effective chiral synthon for the synthesis of chiral bioactive derivatives such as ipsdienol and sodium cilastatin. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9735 / 9738

页数：4

共 25 条

[1]

*ALDR CAT, 1996, HDB FIN CHEM, P582

[2] AN ASYMMETRIC SIMMONS-SMITH REACTION [J].