A new stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts

被引：47

作者：

Li, GG ^{[1
]}

Wei, HX ^{[1
]}

Willis, S ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(98)00850-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method has been developed for the stereospecific synthesis of unusual (Z)-beta-branched Baylis-Hillman adducts with high Z/E selectivity (>99 %) in modest to good yields. The process involves successful formation of anionic beta-substituted [alpha-(alkoxycarbonyl)vinyl]aluminum intermediates and their coupling with aldehydes and ketones catalyzed by n-Bu2BOTf at -78 degrees C. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4607 / 4610

页数：4

共 15 条

[1]

AGGARWAL V, 1996, J CHEM SOC CHEM COMM, P2713

[2] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[3] The asymmetric Baylis-Hillman reaction [J].

Brzezinski, LJ ;

Rafel, S ;

Leahy, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4317-4318

[4]

Ciganek E., 1997, ORG REACTIONS, V51, P201

[5] INTRAMOLECULAR BAYLIS-HILLMAN REACTION - A PATHWAY TO SUBSTITUTED COUMARINS [J].

DREWES, SE ;

NJAMELA, OL ;

EMSLIE, ND ;

RAMESAR, N ;

FIELD, JS .

SYNTHETIC COMMUNICATIONS, 1993, 23 (20) :2807-2815

[6]

GENISSON Y, 1996, J CHEM SOC P1, P2860

[7]

LI G, UNPUB SYNLETT

[8]

Li G-M, UNPUB

[9] CHEMISTRY OF SUBSTITUTED (ALPHA-CARBETHOXYVINYL)CUPRATES .2. STEREOSPECIFIC OLEFIN SYNTHESIS [J].

MARINO, JP ;

LINDERMAN, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4621-4628

[10] Catalytic enantioselective Baylis-Hillman reactions. Correlation between pressure and enantiomeric excess [J].

Marko, IE ;

Giles, PR ;

Hindley, NJ .

TETRAHEDRON, 1997, 53 (03) :1015-1024

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