The conjugate addition-aldol tandem reaction of α,β-unsaturated esters catalyzed by lithium benzenethiolate

被引：67

作者：

Ono, M ^{[1
]}

Nishimura, K ^{[1
]}

Nagaoka, Y ^{[1
]}

Tomioka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(98)02664-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of alpha,beta-unsaturated esters with aldehydes were catalyzed by 0.2 equiv of lithium benzenethiolate in the presence of phenyl trimethylsilyl sulfide to afford the conjugate addition-aldol tandem reaction products in the anti stereoselectivity and good to high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1509 / 1512

页数：4

共 26 条

[1] 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
[2] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
Basavaiah, D
Rao, PD
Hyma, RS
[J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
[3] The asymmetric Baylis-Hillman reaction
Brzezinski, LJ
Rafel, S
Leahy, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) : 4317 - 4318
[4] Ciganek E., 1997, ORG REACTIONS, V51, P201
[5] C-2-symmetric tin(II) complexes as chiral Lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters
Evans, DA
MacMillan, DWC
Campos, KR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10859 - 10860
[6] Enantioselective addition of enol silyl ethers to imines catalyzed by palladium complexes: A novel way to optically active acylalanine derivatives
Hagiwara, E
Fujii, A
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) : 2474 - 2475
[7] ALDOL REACTION OF ALUMINUM ENOLATE RESULTING FROM 1,4-ADDITION OF R2ALX TO ALPHA,BETA-UNSATURATED CARBONYL COMPOUND - A 1-ACYLETHENYL ANION EQUIVALENT
ITOH, A
OZAWA, S
OSHIMA, K
NOZAKI, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (01) : 274 - 278
[8] Stereoselective Michael/aldol tandem reaction triggered by thiolate anion or analogues
Kamimura, A
Mitsudera, H
Asano, S
Kakehi, A
Noguchi, M
[J]. CHEMICAL COMMUNICATIONS, 1998, (10) : 1095 - 1096
[9] A microencapsulated Lewis acid. A new type of polymer-supported Lewis acid catalyst of wide utility in organic synthesis
Kobayashi, S
Nagayama, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) : 2985 - 2986
[10] MCCOMBIE SW, 1993, TETRAHEDRON, V46, P8073

← 1 2 3 →