Enantioselective Claisen rearrangement of difluorovinyl allyl ethers

被引：25

作者：

Ito, H ^{[1
]}

Sato, A ^{[1
]}

Kobayashi, T ^{[1
]}

Taguchi, T ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Tokyo 1920392, Japan

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 22期

关键词：

D O I：

10.1039/a807157h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective Claisen rearrangement of difluorovinyl allyl ethers was achieved, for the first time, in moderate to good enantioselectivity using a chiral boron reagent as the Lewis acid.

引用

页码：2441 / 2442

页数：2

共 17 条

[1] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ACHIRAL ALLYLIC ESTERS [J].

COREY, EJ ;

LEE, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4026-4028

[2] First enantioselective total synthesis of a naturally occurring dolabellane. Revision of absolute configuration [J].

Corey, EJ ;

Kania, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1229-1230

[3] PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].

COREY, EJ ;

IMWINKELRIED, R ;

PIKUL, S ;

XIANG, YB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495

[4]

Filler R., 1993, ORGANOFLUORINE COMPO

[5]

Filler R., 1982, Biomedicinal Aspects of Fluorine Chemistry

[6] FLUORINE-CONTAINING ORGANOZINC REAGENTS .4. THE REFORMATSKII-CLAISEN REACTION OF CHLORODIFLUOROACETIC ACID-DERIVATIVES [J].

GREUTER, H ;

LANG, RW ;

ROMANN, AJ .

TETRAHEDRON LETTERS, 1988, 29 (27) :3291-3294

[7] Enantioselective aromatic Claisen rearrangement [J].

Ito, H ;

Sato, A ;

Taguchi, T .

TETRAHEDRON LETTERS, 1997, 38 (27) :4815-4818

[8] SYNTHESIS CHIRAL GAMMA,DELTA-UNSATURATED AMINO-ACIDS BY ASYMMETRIC ESTER ENOLATE CLAISEN REARRANGEMENT [J].

KAZMAIER, U ;

KREBS, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (18) :2012-2014

[9] The asymmetric ester enolate Claisen rearrangement as a suitable method for the synthesis of sterically highly demanding amino acids [J].

Krebs, A ;

Kazmaier, U .

TETRAHEDRON LETTERS, 1996, 37 (44) :7945-7946

[10] MOLECULAR DESIGN OF A CHIRAL LEWIS-ACID FOR THE ASYMMETRIC CLAISEN REARRANGEMENT [J].

MARUOKA, K ;

SAITO, S ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :1165-1166

← 1 2 →