AN UNUSUAL ENANTIOSELECTIVE ALDOL-TYPE REACTION OF ACETATE BORYL ENOLATE DERIVED FROM CHIRAL THIOIMIDE

被引：30

作者：

YAN, TH

HUNG, AW

LEE, HC

CHANG, CS

机构：

[1] Department of Chemistry, National Chung-Hsing University, Taiwan 400, Taichung

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 26期

关键词：

D O I：

10.1021/jo00105a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The camphor-derived N-acetyloxazolidinethione has been used to effect enantioselective aldol type reactions of the derived 9-BBN enolate with a variety of aldehydes. Mechanistically, the observed facial selectivity is best explained by a boatlike transition structure.

引用

收藏

页码：8187 / 8191

页数：5

相关论文

共 37 条

[1] METAL-ASSISTED ALDOL CONDENSATION OF CHIRAL ALPHA-HALOGENATED IMIDE ENOLATES - A STEREOCONTROLLED CHIRAL EPOXIDE SYNTHESIS [J].

ABDELMAGID, A ;

PRIDGEN, LN ;

EGGLESTON, DS ;

LANTOS, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4595-4602

[2] STEREOSELECTIVE ALDOL REACTIONS WITH ALPHA-UNSUBSTITUTED CHIRAL ENOLATES [J].

BRAUN, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :24-37

[3]

BRAUN M, 1987, ANGEW CHEM, V99, P24

[4] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[5] CONFORMATIONAL-ANALYSIS OF THE IRON ACETYL COMPLEX [(N5-C5H5)FE(CO)(PPH3)COCH3] [J].

DAVIES, SG ;

SEEMAN, JI ;

WILLIAMS, IH .

TETRAHEDRON LETTERS, 1986, 27 (05) :619-622

[6] ASYMMETRIC BORON-CATALYZED REACTIONS [J].

DELOUX, L ;

SREBNIK, M .

CHEMICAL REVIEWS, 1993, 93 (02) :763-784

[7] ENANTIOSELECTIVE SYNTHESES WITH TITANIUM-CARBOHYDRATE COMPLEXES .2. ENANTIOSELECTIVE ALDOL REACTION OF TERT-BUTYL ACETATE USING TITANIUM-CARBOHYDRATE COMPLEXES [J].

DUTHALER, RO ;

HEROLD, P ;

LOTTENBACH, W ;

OERTLE, K ;

RIEDIKER, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04) :495-497

[8]

DUTHALER RO, 1989, ANGEW CHEM INT EDIT, V101, P490

[9] ENANTIOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES - A STERIC MODEL FOR ASYMMETRIC INDUCTION [J].

EVANS, DA ;

TABER, TR .

TETRAHEDRON LETTERS, 1980, 21 (49) :4675-4678

[10] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

NELSON, JV ;

VOGEL, E ;

TABER, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111

← 1 2 3 4 →