The enantioselective chalcogeno-Baylis-Hillman reaction using a chiral hydroxy chalcogenide-TiCl4 complex

被引：47

作者：

Kataoka, T ^{[1
]}

Iwama, T ^{[1
]}

Tsujiyama, S ^{[1
]}

Kanematsu, K ^{[1
]}

Iwamura, T ^{[1
]}

Watanabe, S ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5028585, Japan

来源：

CHEMISTRY LETTERS | 1999年 / 03期

关键词：

D O I：

10.1246/cl.1999.257

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective chalcogeno-Baylis-Hillman reaction was investigated by the use of chiral hydroxy chalcogenides in the presence of TiCl4 under atmospheric pressure. The best result was obtained with 10-methylthioisobornenol as a chiral hydroxy chalcogenide.

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页码：257 / 258

页数：2

相关论文

共 13 条

[1]

ARAI Y, 1990, SYNTHESIS-STUTTGART, P320

[2] Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].

Barrett, AGM ;

Cook, AS ;

Kamimura, A .

CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534

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

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

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

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

Brzezinski, LJ ;

Rafel, S ;

Leahy, JW .

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

[5]

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

[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]

GOODRIDGE RJ, 1988, J ORG CHEM, V53, P2881

[8] An enantioselective Baylis-Hillman reaction catalyzed by chiral phosphines under atmospheric pressure [J].

Hayase, T ;

Shibata, T ;

Soai, K ;

Wakatsuki, Y .

CHEMICAL COMMUNICATIONS, 1998, (12) :1271-1272

[9] The chalcogeno-Baylis-Hillman reaction: the first examples catalysed by chalcogenides in the presence of Lewis acids [J].

Kataoka, T ;

Iwama, T ;

Tsujiyama, S .

CHEMICAL COMMUNICATIONS, 1998, (02) :197-198

[10]

Kataoka T, 1998, TETRAHEDRON, V54, P11813, DOI 10.1016/S0040-4020(98)83041-X