Silica-Immobilized Chiral Dirhodium(II) Catalyst for Enantioselective Carbenoid Reactions

被引：63

作者：

Chepiga, Kathryn M. ^{[1
]}

Feng, Yan ^{[2
]}

Brunelli, Nicholas A. ^{[2
]}

Jones, Christopher W. ^{[2
]}

Davies, Huw M. L. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

[2] Georgia Inst Technol, Sch Chem & Biomol Engn, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 24期

基金：

美国国家科学基金会;

关键词：

C-H ACTIVATION; ASYMMETRIC DIHYDROXYLATION; DONOR/ACCEPTOR CARBENOIDS; TANDEM YLIDE; REARRANGEMENT; CYCLOPROPANATION; SCOPE; FUNCTIONALIZATION; INSERTION; STRATEGY;

D O I：

10.1021/ol403006r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A silica-supported dirhodium(II)tetraprolinate catalyst was synthesized in four steps from L-proline and used in a range of enantioselective transformations of donor/acceptor carbenoids. These include cyclopropenation, cyclopropanation, tandem ylide formation/[2,3] sigmatropic rearrangement, and a variety of combined C-H functionalization/Cope rearrangement reactions. The products of these transformations were obtained in yields and levels of enantioselectivity comparable to those obtained with its homogeneous counterpart, Rh-2(S-DOSP)(4). The silica-supported Rh-2(S-DOSP)(4) derivative was successfully recycled over five reactions.

引用

页码：6136 / 6139

页数：4

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