Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols

被引：3

作者：

Kawashima, Yuya ^{[1
]}

Ezawa, Tetsuya ^{[1
]}

Yamamura, Mai ^{[1
]}

Harada, Taisuke ^{[1
]}

Noguchi, Takuya ^{[1
]}

Miura, Tsuyoshi ^{[2
]}

Imai, Nobuyuki ^{[1
]}

机构：

[1] Chiba Inst Sci, Fac Pharm, Choshi, Chiba 2880025, Japan

[2] Tokyo Univ Pharm & Life Sci, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON | 2015年 / 71卷 / 45期

基金：

日本学术振兴会;

关键词：

Enantioselectivity; Simmons-Smith cyclopropanation; Fluorous disulfonamide; Chiral ligand; Recycle; BIS(HALOMETHYL)ZINC REAGENTS; WATER; COMPLEX; OLEFINS; SYSTEM; ACID;

D O I：

10.1016/j.tet.2015.09.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylic alcohols reacted with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49-85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：8585 / 8592

页数：8

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