A copper-catalyzed method for the facially selective addition of Grignard reagents to cyclopropenes

被引：88

作者：

Liao, LA ^{[1
]}

Fox, JM ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 48期

关键词：

D O I：

10.1021/ja0278234

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Cu-catalyzed method for the addition of Grignard reagents to 1-alkyl-3-hydroxymethylcyclopropenes and their MOM ethers is described. The face of addition is syn relative to the hydroxymethyl and alkoxymethyl groups. Excellent diastereoselectivity is observed for a range of alkyl, alkenyl, and alkynylmagnesium halides. The addition reactions create chiral all-carbon quaternary centers, and the cyclopropylmetals that are generated can be reacted with electrophiles to produce highly functionalized cyclopropanes. Copyright © 2002 American Chemical Society.

引用

页码：14322 / 14323

页数：2

共 33 条

[1]

[Anonymous], COMPREHENSIVE ORGANI

[2]

Araki S, 2001, CHEM-EUR J, V7, P2784, DOI 10.1002/1521-3765(20010702)7:13<2784::AID-CHEM2784>3.0.CO

[3]

2-A

[4] Stereodivergent allylindation of cyclopropenes. Remarkable stereodirection and acceleration by neighbouring carboxyl and hydroxyl groups [J].

Araki, S ;

Nakano, H ;

Subburaj, K ;

Hirashita, T ;

Shibutani, K ;

Yamamura, H ;

Kawai, M ;

Butsugan, Y .

TETRAHEDRON LETTERS, 1998, 39 (35) :6327-6330

[5]

BAIRD MS, 1996, CARBOCYCLIC 3 MEMBER, P114

[6]

BAIRD MS, 1988, TOP CURR CHEM, V144, P139

[7]

Charette A.B., 2001, ORG REACT, V58, P1, DOI DOI 10.1002/0471264180.OR058.01

[8]

Charette A. B., 1999, COMPREHENSIVE ASYMME, V2, P581

[9] First evidence for the formation of a geminal dizinc carbenoid: A highly stereoselective synthesis of 1,2,3-substituted cyclopropanes [J].

Charette, AB ;

Gagnon, A ;

Fournier, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :386-387

[10] Diastereo- and enantioselective synthesis of 1,2,3-substituted cyclopropanes with zinc carbenoids [J].

Charette, AB ;

Lemay, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (10) :1090-1092

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