BiCl3-catalyzed Mukaiyama-aldol and carbonyl-ene reactions

被引：33

作者：

Peidro, L ^{[1
]}

LeRoux, C ^{[1
]}

Laporterie, A ^{[1
]}

Dubac, J ^{[1
]}

机构：

[1] UNIV TOULOUSE 3,CNRS,URA 477,F-31062 TOULOUSE,FRANCE

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1996年 / 521卷 / 1-2期

关键词：

Bi catalysis; Mukaiyama-aldol reaction;

D O I：

10.1016/0022-328X(96)06229-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The H-ene pathway has not been detected for the bismuth(III) chloride-catalyzed Mukaiyama-aldol reaction involving silyl enol ethers and aldehydes. The silatropic ene-like process is the only mechanism observed, even with the weakly reactive 1-(trimethylsilyloxy) cyclohexene. However, trimerization of an aliphatic aldehyde can occur.

引用

收藏

页码：397 / 399

页数：3

相关论文

共 28 条

[1]

ABEL EW, 1975, J ORGANOMET CHEM, V84, P199, DOI 10.1016/S0022-328X(00)90032-9

[2] CATION EXCHANGE RESIN-CATALYZED CONDENSATION AND POLYMERIZATION OF ALDEHYDES AND CYCLOHEXANONE [J].

ASTLE, MJ ;

PINNS, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (01) :56-60

[3] LEWIS ACID CATALYSIS OF THE ENE ADDITION OF CHLORAL AND BROMAL TO OLEFINS - PRODUCT STUDIES [J].

BENNER, JP ;

GILL, GB ;

PARROTT, SJ ;

WALLACE, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :291-313

[4] LEWIS ACID CATALYSIS OF THE ENE ADDITION OF CHLORAL AND BROMAL TO OLEFINS - STEREOCHEMICAL AND MECHANISTIC STUDIES [J].

BENNER, JP ;

GILL, GB ;

PARROTT, SJ ;

WALLACE, B ;

BEGLEY, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03) :315-329

[5]

COSSU M, 1973, CR ACAD SCI C CHIM, V277, P1145

[6] YB(FOD)3-PROMOTED ENE REACTION OF ALDEHYDES WITH VINYL ETHERS [J].

DEATON, MV ;

CIUFOLINI, MA .

TETRAHEDRON LETTERS, 1993, 34 (15) :2409-2412

[7]

DENMARK SE, 1992, TETRAHEDRON, V48, P5565

[8] ENE AND RETRO-ENE REACTIONS IN GROUP-14 ORGANOMETALLIC CHEMISTRY [J].

DUBAC, J ;

LAPORTERIE, A .

CHEMICAL REVIEWS, 1987, 87 (02) :319-334

[9]

Fleming I., 1989, ORG REACTIONS, V37, P57

[10] ASYMMETRIC INDUCTION IN ENE REACTION OF CHLORAL WITH (1S,5S)-(-)-BETA-PINENE - CONTROL OF STEREOSELECTIVITY BY CHOICE OF LEWIS ACID CATALYST [J].

GILL, GB ;

WALLACE, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (11) :382-383