One-pot synthesis of epoxides from benzyl alcohols and aldehydes

被引：7

作者：

Alfonzo, Edwin ^{[1
]}

Mendoza, Jesse W. L. ^{[1
]}

Beeler, Aaron B. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, 590 Commonwealth Ave, Boston, MA 02215 USA

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 14卷

基金：

美国国家科学基金会;

关键词：

Corey-Chaykovsky; epoxide; heterocycle; one-pot; ylide; MEINWALD REARRANGEMENT REACTIONS; CARBONYL REARRANGEMENT; ASYMMETRIC-SYNTHESIS; GUANIDINE BASES; EPOXIDATION; SCOPE; ACID; OXIDATION; OXIRANES; COMPLEX;

D O I：

10.3762/bjoc.14.205

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey-Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.

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页码：2308 / 2312

页数：5

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