The vinylogous intramolecular Morita-Baylis-Hillman reaction: Synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts

被引：219

作者：

Frank, SA ^{[1
]}

Mergott, DJ ^{[1
]}

Roush, WR ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 11期

关键词：

D O I：

10.1021/ja017123j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of the vinylogous intramolecular Morita-Baylis-Hillman reaction for the synthesis of functionalized cyclopentenes and cyclohexenes is described. The reaction involves the trialkyphosphine-catalyzed cyclization of 1,6- or 1,7-diactivated 1,5-hexadienes or 1,6-heptadienes, containing carboxyaldehyde, methyl ketone, or methoxycarbonyl as the olefin activating groups. A representative example of this reaction is the Me3P-catalyzed cyclization of 1a in tert-amyl alcohol, which provides the substituted cyclopentene 2a in 95% yield and with 97:3 regioselectivity. Copyright © 2002 American Chemical Society.

引用

收藏

页码：2404 / 2405

页数：2

相关论文

共 20 条

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

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

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

[2] DABCO CATALYZED DIMERIZATION OF ALPHA,BETA-UNSATURATED KETONES AND NITRILES [J].

BASAVAIAH, D ;

GOWRISWARI, VVL ;

BHARATHI, TK .

TETRAHEDRON LETTERS, 1987, 28 (39) :4591-4592

[3] An intramolecular Baylis-Hillman reaction catalysed by secondary amines [J].

Black, GP ;

Dinon, F ;

Fratucello, S ;

Murphy, PJ ;

Nielsen, M ;

Williams, HL .

TETRAHEDRON LETTERS, 1997, 38 (49) :8561-8564

[4]

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

[5] Tandem Michael/intramolecular aldol reactions mediated by secondary amines, thiols and phosphines [J].

Dinon, F ;

Richards, E ;

Murphy, PJ ;

Hibbs, DE ;

Hursthouse, MB ;

Abdul Malik, KM .

TETRAHEDRON LETTERS, 1999, 40 (16) :3279-3282

[6] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].

DREWES, SE ;

ROOS, GHP .

TETRAHEDRON, 1988, 44 (15) :4653-4670

[7] 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

[8] DABCO-CATALYZED DIMERIZATION OF SOME ALPHA,BETA-UNSATURATED ESTERS [J].

DREWES, SE ;

EMSLIE, ND ;

KARODIA, N .

SYNTHETIC COMMUNICATIONS, 1990, 20 (13) :1915-1921

[9] The kinetics and mechanism of the phosphorus-catalysed dimerisation of acrylonitrile [J].

Hall, CD ;

Lowther, N ;

Tweedy, BR ;

Hall, AC ;

Shaw, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (09) :2047-2054

[10]

HWU JR, 1992, TETRAHEDRON LETT, V33, P6469