Hydroxy-Directed Cyclopropanation of Esters: Synthesis of Trisubstituted Cyclopropanols

被引：14

作者：

Astashko, Dmitry ^{[1
]}

Cha, Jin Kun ^{[1
]}

Rao, Nagavaram Narsimha ^{[1
]}

Parida, Bibhuti Bhusan ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 01期

基金：

美国国家科学基金会;

关键词：

Small ring systems; Allylic compounds; Titanium; Grignard reaction; Synthetic methods; REAGENTS SELECTIVITY ISSUES; ALLYL-TRANSFER REACTION; KULINKOVICH CYCLOPROPANATION; DIASTEREOSELECTIVE SYNTHESIS; TITANIUM(IV) ALKOXIDES; ETHYLMAGNESIUM BROMIDE; HOMOALLYL ALCOHOLS; ALKENES; ALKYLATION; ALDEHYDES;

D O I：

10.1002/ejoc.201301252

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Kulinkovich cyclopropanation of esters with disubstituted homoallylic alcohols is described for the preparation of 1,2,3-trisubstituted cyclopropanols. Central to the successful implementation is the generation in situ of a temporary alkoxy tether between a homoallylic alcohol and an alkoxytitanium species to override unfavorable steric factors.

引用

页码：181 / 187

页数：7

共 42 条

[1] Stereochemistry of the Kulinkovich Cyclopropanation of Nitriles [J].