A new chiral disulfonamide ligand derived from alpha-amino acid for catalytic enantioselective cyclopropanation

被引：49

作者：

Imai, N

Sakamoto, K

Maeda, M

Kouge, K

Yoshizane, K

Nokami, J

机构：

[1] Faculty of Engineering, Okayama University of Science, Okayama 700

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(97)00038-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new disulfonamide prepared from alpha-amino acid in five steps catalyzed cyclopropanation of allylic alcohols with Et(2)Zn and CH2I2 to afford the corresponding cyclopropylmethanols in moderate to good enantioselectivites. In particular, the reaction of cinnamyl alcohol in the presence of a chiral disulfonamide 1k afforded an excellent enantioselectivity (85% ee). (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：1423 / 1426

页数：4

相关论文

共 16 条

[1] IMPROVED PROCEDURE FOR THE SYNTHESIS OF ENANTIOMERICALLY ENRICHED CYCLOPROPYLMETHANOL DERIVATIVES [J].

CHARETTE, AB ;

PRESCOTT, S ;

BROCHU, C .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :1081-1083

[2] THE USE OF ALPHA-D-GLUCOPYRANOSIDES AS SURROGATES FOR THE BETA-L-GLUCOPYRANOSIDES IN THE STEREOSELECTIVE CYCLOPROPANATION REACTION [J].

CHARETTE, AB ;

TURCOTTE, N ;

MARCOUX, JF .

TETRAHEDRON LETTERS, 1994, 35 (04) :513-516

[3] THE USE OF 1,2-TRANS-CYCLOHEXANEDIOL AS AN EFFICIENT CHIRAL AUXILIARY FOR THE ASYMMETRIC CYCLOPROPANATION OF ALLYLIC ETHERS [J].

CHARETTE, AB ;

MARCOUX, JF .

TETRAHEDRON LETTERS, 1993, 34 (45) :7157-7160

[4] CARBOHYDRATES AS CHIRAL AUXILIARIES - ASYMMETRIC CYCLOPROPANATION REACTION OF ACYCLIC OLEFINS [J].

CHARETTE, AB ;

COTE, B ;

MARCOUX, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8166-8167

[5] A NEW STRATEGY FOR THE LEWIS ACID-CATALYZED CYCLOPROPANATION OF ALLYLIC ALCOHOLS [J].

CHARETTE, AB ;

BROCHU, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (45) :11367-11368

[6]

CHARETTE AB, 1994, J AM CHEM SOC, V116, P8166

[7] CATALYTIC ENANTIOSELECTIVE CYCLOPROPANATION WITH BIS(HALOMETHYL)ZINC REAGENTS .2. THE EFFECT OF PROMOTER STRUCTURE ON SELECTIVITY [J].

DENMARK, SE ;

CHRISTENSON, BL ;

OCONNOR, SP .

TETRAHEDRON LETTERS, 1995, 36 (13) :2219-2222

[8] CATALYTIC ENANTIOSELECTIVE CYCLOPROPANATION WITH BIS(HALOMETHYL)ZINC REAGENTS .1. OPTIMIZATION OF REACTION PROTOCOL [J].

DENMARK, SE ;

CHRISTENSON, BL ;

COE, DM ;

OCONNOR, SP .

TETRAHEDRON LETTERS, 1995, 36 (13) :2215-2218

[9] STRUCTURE OF CURACIN-A, A NOVEL ANTIMITOTIC, ANTIPROLIFERATIVE, AND BRINE SHRIMP TOXIC NATURAL PRODUCT FROM THE MARINE CYANOBACTERIUM LYNGBYA-MAJUSCULA [J].

GERWICK, WH ;

PROTEAU, PJ ;

NAGLE, DG ;

HAMEL, E ;

BLOKHIN, A ;

SLATE, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1243-1245

[10] ENANTIOSELECTIVE CYCLOPROPANATION OF ALLYLIC ALCOHOLS CATALYZED BY A CHIRAL DISULFONAMIDE-ALUMINUM COMPLEX [J].

IMAI, N ;

TAKAHASHI, H ;

KOBAYASHI, S .

CHEMISTRY LETTERS, 1994, (01) :177-180