CYCLOPROPANE DERIVATIVES .3. (1-ALKYLCYCLOPROPYL)KETONES BY ACYLATION OF ALPHA-SUBSTITUTED GAMMA-LACTONES

被引：9

作者：

BOHRER, G ^{[1
]}

BOHRER, P ^{[1
]}

KNORR, R ^{[1
]}

机构：

[1] UNIV MUNICH,INST ORGAN CHEM,KARLSTR 23,W-8000 MUNICH 2,GERMANY

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 11期

关键词：

Acylation; Butanolides; Cyclopropyl compounds; Ketones; γ‐Lactones;

D O I：

10.1002/cber.19901231113

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclopropane Derivatives, 3. — (1‐Alkylcyclopropyl)ketones by Acylation of α‐Substituted γ‐Lactones The 2‐acylation of 2‐substituted 4‐butanolides 2 is moderately sensitive to steric crowding, whereas the subsequent ring‐ opening of 2‐acyl‐2‐alkyl‐4‐butanolides 4, 11 to give‐chloro ketones 6, 12 by chloride‐transferring acid derivatives be‐comes difficult with bigger lactone substituents. Similar observations pertain to the preparation of y‐chlorobutanoyl chlorides 10 from 2‐alkyl‐4‐butanolides 2. The proper choice of the starting 4‐butanolides (2a, b or 14 but not 2c) provides for an indirect coupling of two different lactones to y,y‐dichloro ke‐tones 12. Dicyclopropyl ketones 13 with variable patterns of substitution may thus be prepared from 4‐butanolides in a direct manner with global yields exceeding 50% and without purification of intermediate products (except for acid chlorides like 10). Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

引用

页码：2167 / 2172

页数：6

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