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

被引：30

作者：

Kobayashi, S ^{[1
]}

Akiyama, R ^{[1
]}

Moriwaki, M ^{[1
]}

机构：

[1] JAPAN SCI & TECHNOL CORP,CREST,SHINJUKU KU,TOKYO 162,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(97)01041-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various gamma-acyl-delta-lactam derivatives were prepared on the basis of three-component (silyl enolates, alpha,beta-unsaturated thioesters, and imines) or four-component (silyl enolates, alpha,beta-unsaturated thioesters, amines, and aldehydes) coupling reactions via Lewis acid-catalyzed tandem Michael-imino aldol reactions. (C) 1997 Elsevier Science Ltd.

引用

页码：4819 / 4822

页数：4

共 26 条

[1] Multiple-component condensation strategies for combinatorial library synthesis
Armstrong, RW
Combs, AP
Tempest, PA
Brown, SD
Keating, TA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) : 123 - 131
[2] BIOSYNTHESIS OF STRYCHNINE
HEIMBERG.SI
SCOTT, AI
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (06) : 217 - 218
[3] TOTAL SYNTHESIS OF (+/-)-SURUGATOXIN
INOUE, S
OKADA, K
TANINO, H
HASHIZUME, K
KAKOI, H
[J]. TETRAHEDRON LETTERS, 1984, 25 (39) : 4407 - 4410
[4] KOBAYASHI S, 1994, SYNLETT, P689
[5] THE STEREOSELECTIVE MICHAEL REACTION OF ALPHA, BETA-UNSATURATED THIOESTERS WITH SILYL ENOL ETHERS PROMOTED BY COMBINED USE OF ANTIMONY(V) CHLORIDE AND TIN(II) TRIFLATE
KOBAYASHI, S
TAMURA, M
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1988, (01) : 91 - 94
[6] SCANDIUM TRIFLUOROMETHANESULFONATE (SC(OTF)3) - A NOVEL REUSABLE CATALYST IN THE DIELS-ALDER REACTION
KOBAYASHI, S
HACHIYA, I
ARAKI, M
ISHITANI, H
[J]. TETRAHEDRON LETTERS, 1993, 34 (23) : 3755 - 3758
[7] LN(OTF)3-CATALYZED OR SC(OTF)(3)-CATALYZED 3 COMPONENTS COUPLING REACTIONS BETWEEN ALDEHYDES, AMINES, AND DIENES OR ALKENES - EFFICIENT SYNTHESES OF PYRIDINE AND QUINOLINE DERIVATIVES
KOBAYASHI, S
ISHITANI, H
NAGAYAMA, S
[J]. CHEMISTRY LETTERS, 1995, (06) : 423 - 424
[8] KOBAYASHI S, 1995, TETRAHEDRON LETT, V36, P5773, DOI 10.1016/00404-0399(50)1096Z-
[9] THE TRITYL PERCHLORATE CATALYZED MICHAEL REACTION
KOBAYASHI, S
MURAKAMI, M
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1985, (07) : 953 - 956
[10] KOJIMA R, 1970, Chemical and Pharmaceutical Bulletin (Tokyo), V18, P2555

← 1 2 3 →