Guide to enantioselective dirhodium(II)-catalyzed cyclopropanation with aryldiazoacetates

被引：35

作者：

Chepiga, Kathryn M. ^{[1
]}

Qin, Changming ^{[1
]}

Alford, Joshua S. ^{[1
]}

Chennamadhavuni, Spandan ^{[1
]}

Gregg, Timothy M. ^{[2
]}

Olson, Jeremy P. ^{[1
]}

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

机构：

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

[2] Canisius Coll, Dept Chem & Biochem, Buffalo, NY 14208 USA

来源：

TETRAHEDRON | 2013年 / 69卷 / 27-28期

基金：

美国国家卫生研究院;

关键词：

Asymmetric cyclopropanation; Cyclopropanes; Donor/acceptor carbenoids; Dirhodium catalysis; Phenyldiazoacetate; SUBSTITUTED RHODIUM CARBENOIDS; ASYMMETRIC-SYNTHESIS; TURNOVER NUMBERS; HIGHLY EFFICIENT; CATALYST; CYCLOADDITION; STEREOSELECTIVITY; ESTERS;

D O I：

10.1016/j.tet.2013.04.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic enantioselective methods for the generation of cyclopropanes have been of long standing pharmaceutical interest. Chiral dirhodium(II) catalysts prove to be an effective means for the generation of diverse cyclopropane libraries. Rh-2(R-DOSP)(4) is generally the most effective catalyst for asymmetric intermolecular cyclopropanation of methyl aryldiazoacetates with styrene. Rh-2(S-PTAD)(4) provides high levels of enantioinduction with ortho-substituted aryldiazoacetates. The less-established Rh-2(R-BNP)(4) plays a complementary role to Rh-2(R-DOSP)(4) and Rh-2(S-PTAD)(4) in catalyzing highly enantioselective cyclopropanation of 3-methoxy substituted aryldiazoacetates. Substitution on the styrene has only moderate influence on the asymmetric induction of the cyclopropanation. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5765 / 5771

页数：7

共 32 条

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