Tandem Mukaiyama Michael-aldol reactions catalysed by samarium diiodide

被引：34

作者：

Giuseppone, N ^{[1
]}

Collin, J ^{[1
]}

机构：

[1] Univ Paris 11, Inst Chim Mol Orsay, ESA 8075, Lab Catalyse Mol, F-91405 Orsay, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 43期

关键词：

samarium diiodide catalysis; tandem reactions; Michael reactions; aldol reactions;

D O I：

10.1016/S0040-4020(01)00902-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samarium diiodide is an efficient precatalyst for tandem Michael-aldol reactions, which allow the formation of two carbon-carbon bonds by successive additions of a ketene silyl acetal and an aldehyde on cyclic alpha,beta -unsaturated ketones. The adducts are isolated as silyl ethers, in good yields, and in some cases with high diastereoselectivities when the reactions are performed at low temperatures. Comparative study of the activities of other lanthanide iodides for the same tandem reactions is presented. A key step for a formal synthesis of PGF(2 alpha) has been performed by a tandem Michael-aldol samarium-catalysed sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8989 / 8998

页数：10

共 89 条

[31] A HIGHLY STEREOSELECTIVE SYNTHESIS OF GAMMA-ACYL-DELTA-LACTONES BY THE TRITYL PERCHLORATE CATALYZED TANDEM MICHAEL-ALDOL REACTION
KOBAYASHI, S
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1986, (11) : 1805 - 1808
[32] A NOVEL MANNICH-TYPE REACTION IN AQUEOUS-MEDIA - LANTHANIDE TRIFLATE-CATALYZED CONDENSATION OF ALDEHYDES, AMINES AND VINYL ETHERS FOR THE SYNTHESIS OF BETA-AMINO KETONES
KOBAYASHI, S
ISHITANI, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) : 1379 - 1379
[33] KOBAYASHI S, 1995, TETRAHEDRON LETT, V36, P5773, DOI 10.1016/00404-0399(50)1096Z-
[34] Kobayashi S, 1999, EUR J ORG CHEM, V1999, P15
[35] Kobayashi S, 1997, CHEM LETT, P1039
[36] TRITYL PERCHLORATE CATALYZED TANDEM MICHAEL-ALDOL REACTION - A FACILE METHOD FOR THE STEREOSELECTIVE SYNTHESES OF GAMMA-ACYL SUBSTITUTED SIGMA-HYDROXY KETONE DERIVATIVES
KOBAYASHI, S
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1986, (02) : 221 - 224
[37] Three-component or four-component coupling reactions leading to delta-lactams. Facile synthesis of gamma-acyl-delta-lactams from silyl enolates, alpha,beta-unsaturated thioesters, and imines or amines and aldehydes via tandem Michael-imino aldol reactions
Kobayashi, S
Akiyama, R
Moriwaki, M
[J]. TETRAHEDRON LETTERS, 1997, 38 (27) : 4819 - 4822
[38] An expedient route for the stereoselective construction of bridged polyheterocyclic ring systems using the tandem ''pincer'' Diels-Alder reaction
Lautens, M
Fillion, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) : 4418 - 4427
[39] LEROUX C, 1993, B SOC CHIM FR, V130, P832
[40] NEW EFFECTIVE CATALYSTS FOR MUKAIYAMA-ALDOL AND MUKAIYAMA-MICHAEL REACTIONS - BICL3-METALLIC IODIDE SYSTEMS
LEROUX, C
GASPARDILOUGHMANE, H
DUBAC, J
JAUD, J
VIGNAUX, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) : 1835 - 1839

← 1 2 3 4 5 6 7 8 9 →