Diastereoselective Borocyclopropanation of Allylic Ethers Using a Boromethylzinc Carbenoid

被引：72

作者：

Benoit, Guillaume ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Stn Downtown, POB 6128, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 04期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

C-H BORYLATION; STEREOSELECTIVE CYCLOPROPANATION; ENANTIOSELECTIVE SYNTHESIS; REAGENTS RXZNCH2Y; ALCOHOLS; 1-ALKENYL-1,1-HETEROBIMETALLICS; PHOSPHATES; GENERATION;

D O I：

10.1021/jacs.6b09090

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A borocyclopropanation of (E)- and (Z)-allylic ethers and styrene derivatives via the Simmons-Smith reaction using a novel boromethylzinc carbenoid is described. The carbenoid precursor is prepared via a 3-step sequence from inexpensive and commercially available starting materials. This methodology allows for the preparation of 1,2,3-substituted borocyclopropanes in high yields and diastereoselectivities. Several postfunctionalization reactions were also performed to illustrate the versatility of these building blocks.

引用

页码：1364 / 1367

页数：4

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