Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base

被引：158

作者：

Barrett, AGM ^{[1
]}

Cook, AS ^{[1
]}

Kamimura, A ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 22期

关键词：

D O I：

10.1039/a806115g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel chiral pyrrolizidine base 5 derived from L-proline promotes the Baylis-Hillman reaction of ethyl and methyl vinyl ketones with electron deficient aromatic aldehydes with moderate levels of enantiomeric excess.

引用

页码：2533 / 2534

页数：2

共 15 条

[1] First-examples of metal and ligand accelerated catalysis of the Baylis-Hillman reaction
Aggarwal, VK
Tarver, GJ
McCague, R
[J]. CHEMICAL COMMUNICATIONS, 1996, (24) : 2713 - 2714
[2] CATALYTIC ASYMMETRIC-SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-KETONES
BARRETT, AGM
KAMIMURA, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (17) : 1755 - 1756
[3] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
Basavaiah, D
Rao, PD
Hyma, RS
[J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
[4] The asymmetric Baylis-Hillman reaction
Brzezinski, LJ
Rafel, S
Leahy, JW
[J]. 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
DREWES, SE
ROOS, GHP
[J]. TETRAHEDRON, 1988, 44 (15) : 4653 - 4670
[7] Grieco P. A., 1991, ALDRICHIM ACTA, V24, P59
[8] GROTE R, 1990, LIEBIGS ANN CHEM, P525
[9] An enantioselective Baylis-Hillman reaction catalyzed by chiral phosphines under atmospheric pressure
Hayase, T
Shibata, T
Soai, K
Wakatsuki, Y
[J]. CHEMICAL COMMUNICATIONS, 1998, (12) : 1271 - 1272
[10] RECENT ADVANCES IN THE SYNTHESIS OF PYRROLIZIDINES
IKEDA, M
SATO, T
ISHIBASHI, H
[J]. HETEROCYCLES, 1988, 27 (06) : 1465 - 1487

← 1 2 →