REACTION OF CYCLOPROPYL KETONES WITH ACETYL METHANESULFONATE - EFFICIENT RING-OPENING UNDER NEUTRAL CONDITIONS WITH REGIOSPECIFIC ENOL ACETATE FORMATION AND STEREO-CONTROLLED NUCLEOPHILIC-ADDITION

被引：31

作者：

DEMUTH, M

RAGHAVAN, PR

机构：

[1] Institut für Strahlenchemie im Max-Planck-Institut für Kohlenforschung, Mülheim A.D. Ruhr

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 07期

关键词：

D O I：

10.1002/hlca.19790620730

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclopropyl ketones are readily cleaved under neutral conditions at room temperature by the combined action of acetyl methanesulfonate and nucleophiles such as Br−, I−, and MsO−. The high‐yield reaction involves regiospecific enol acetate formation with a stereoselectivity of nucleophile addition which is compatible with an SN2‐type opening of the cyclopropyl ring. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：2338 / 2340

页数：3

共 14 条

[1]

COREY EJ, 1973, TETRAHEDRON LETT, P3153

[2]

DANISHEFSKY D, 1979, ACCOUNTS CHEM RES, V12, P66

[3]

Dauben W.G., 1974, TOP CURR, V54, P73

[4]

DEMUTH M, UNPUBLISHED