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
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
收藏
页码:8585 / 8592
页数:8
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