Asymmetric Simmons-Smith cyclopropanation of E-allylic alcohols using 1,1'-bi-2-naphthol-3,3'-dicarboxamide as a chiral auxiliary

被引：62

作者：

Kitajima, H ^{[1
]}

Aoki, Y ^{[1
]}

Ito, K ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] KYUSHU UNIV 33, FAC SCI, DEPT CHEM, HIGASHI KU, FUKUOKA 81281, JAPAN

来源：

CHEMISTRY LETTERS | 1995年 / 12期

关键词：

D O I：

10.1246/cl.1995.1113

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N,N,N'N'-Tetraethyl- 1, 1'-bi-2-naphthol-3,3'-dicarboxamide (1b) was found to be an effective chiral auxiliary for asymmetric Simmons-Smith cyclopropanation and high enantioselectivity greater than 85% ee was achieved in the reaction of E-allylic alcohols.

引用

页码：1113 / 1114

页数：2

共 15 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] DESIGN OF AMPHOTERIC BIFUNCTIONAL LIGANDS - APPLICATION TO THE ENANTIOSELECTIVE SIMMONS-SMITH CYCLOPROPANATION OF ALLYLIC ALCOHOLS [J].

CHARETTE, AB ;

JUTEAU, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2651-2652

[3] 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

[4]

DENMARK SE, 1992, SYNTHESIS-STUTTGART, P229

[5] 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

[6] 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

[7] ASYMMETRIC CYCLOPROPANATION OF 1-ALKENYLBORONIC ESTERS AND ITS APPLICATION TO THE SYNTHESIS OF OPTICALLY-ACTIVE CYCLOPROPANOLS [J].

IMAI, T ;

MINETA, H ;

NISHIDA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :4986-4988

[8] OPTICALLY-ACTIVE CYCLOPROPANES [J].

SALAUN, J .

CHEMICAL REVIEWS, 1989, 89 (05) :1247-1270

[9]

SHIMAMOTO K, 1993, SYNLETT, P919

[10]

STAMMER CH, 1990, TETRAHEDRON, V46, P2231

← 1 2 →