1,13 and 1,14 asymmetric induction: Remote control

被引：28

作者：

Magnus, N

Magnus, P

机构：

[1] Department of Chemistry, University of Texas at Austin, Austin

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 20期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(97)00704-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the acyclic sulfones 6 (n = 1, 2, 3 and 4) with n-BuLI/THF/-100 degrees C followed by PhCHO gave only two diastereomeric beta-hydroxysulfones 7. The selection of two out of a possible four diastereomers is observed even though the chiral inducing entity is 10, 11, 12 and 13 atoms from the reaction locus. These results represent the illustration of long range asymmetric induction (LAI) controlled by supramolecular interactions. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：3491 / 3494

页数：4

相关论文

共 20 条

[1] ASYMMETRIC SUBSTITUTION - HIGHLY ENANTIOSELECTIVE SUBSTITUTIONS INDUCED AT THE CARBANION OF A RACEMIC ORGANOLITHIUM SUBSTRATE BY (-)-SPARTEINE [J].

BEAK, P ;

DU, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2516-2518

[2] THE STRUCTURE OF LITHIUM COMPOUNDS OF SULFONES, SULFOXIMIDES, SULFOXIDES, THIOETHERS AND 1,3-DITHIANES, NITRILES, NITRO-COMPOUNDS AND HYDRAZONES [J].

BOCHE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (03) :277-297

[3] Dilithiated (E)-N-isobutyl-4-tosyl-2-butenamide: An allyl sulfone dianion for the regiospecific gamma-functionalization of crotonamide dianion [J].

Caturla, F ;

Najera, C .

TETRAHEDRON LETTERS, 1996, 37 (27) :4787-4790

[4] AUXILIARY-BASED, ASYMMETRIC SN2' REACTIONS - A CASE OF 1,7-RELATIVE STEREOGENESIS [J].

DENMARK, SE ;

MARBLE, LK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :1984-1986

[5] 1,5-asymmetric induction in methyl ketone aldol addition reactions [J].

Evans, DA ;

Coleman, PJ ;

Cote, B .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :788-789

[6] Concise synthesis of taxol A-ring components: Remote diastereoselective additions of alkenyl lithiums to aldehydes [J].

Frost, C ;

Linnane, P ;

Magnus, P ;

Spyvee, M .

TETRAHEDRON LETTERS, 1996, 37 (51) :9139-9142

[7] ABOUT THE LI+ COUNTERION EFFECT ON ALPHA-SULFONYL CARBANIONS [J].

GAIS, HJ ;

HELLMANN, G ;

LINDNER, HJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1990, 29 (01) :100-103

[8] REMOTE ASYMMETRIC INDUCTION IN REACTIONS BETWEEN 4-BENZYLOXYPENT-2-ENYL(TRIBUTYL)STANNANE AND 5-BENZYLOXYPENT-2-ENYL(TRIBUTYL)STANNANE AND CHIRAL IMINES PREPARED FROM BUTYL GLYOXYLATE [J].

HALLETT, DJ ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (06) :657-658

[9]

Lehn J. M., 1995, SUPRAMOLECULAR CHEM

[10] Induction of molecular asymmetry by a remote chiral group [J].

Linnane, P ;

Magnus, N ;

Magnus, P .

NATURE, 1997, 385 (6619) :799-801