THE TANDEM MICHAEL-S(N)2 REACTION FOR THE CONSTRUCTION OF THE 3-AZABICYCLO[3.1.0]HEXANE RING-SYSTEM

被引：21

作者：

CHAN, S ^{[1
]}

BRAISH, TF ^{[1
]}

机构：

[1] PFIZER INC,DIV CENT RES,PROC RES & DEV,GROTON,CT 06340

来源：

TETRAHEDRON | 1994年 / 50卷 / 33期

关键词：

INTRAMOLECULAR MICHAEL; INTRAMOLECULAR S(N)2; 3-AZABICYCLO[3.1.0]HEXANE; 3-AZABICYCLO[4.1.0]HEPTANE; DICHLOROACETIC ACID;

D O I：

10.1016/S0040-4020(01)89609-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 3-azabicyclo[3.1.0]-hexane ring system was constructed in a convergent one-pot procedure starting from readily available starting materials, using the intramolecular tandem Michael-S(N)2 reaction. The methodology was also extended to the synthesis of 3-azabicyclo[4.1.0]heptane ring system.

引用

收藏

页码：9943 / 9950

页数：8

相关论文

共 28 条

[1] TANDEM MICHAEL REACTIONS FOR THE CONSTRUCTION OF PYRROLIDINE AND PIPERIDINE RING-SYSTEMS [J].

BARCO, A ;

BENETTI, S ;

CASOLARI, A ;

POLLINI, GP ;

SPALLUTO, G .

TETRAHEDRON LETTERS, 1990, 31 (21) :3039-3042

[2] TANDEM MICHAEL REACTIONS FOR THE CONSTRUCTION OF HIGHLY FUNCTIONALIZED 5-MEMBERED RINGS [J].

BUNCE, RA ;

WAMSLEY, EJ ;

PIERCE, JD ;

SHELLHAMMER, AJ ;

DRUMRIGHT, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) :464-466

[3] TANDEM SN2-MICHAEL REACTIONS FOR THE PREPARATION OF SIMPLE 5-MEMBERED AND 6-MEMBERED-RING NITROGEN AND SULFUR HETEROCYCLES [J].

BUNCE, RA ;

PEEPLES, CJ ;

JONES, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1727-1733

[4]

CHAOGUO Y, 1992, SYNTHETIC COMMUN, V12, P1651

[5] ANGIOTENSIN-CONVERTING ENZYME-INHIBITORS - SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ACYL TRIPEPTIDE ANALOGS OF ENALAPRIL [J].

GREENLEE, WJ ;

ALLIBONE, PL ;

PERLOW, DS ;

PATCHETT, AA ;

ULM, EH ;

VASSIL, TC .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (04) :434-442

[6] HETEROCYCLES IN ASYMMETRIC-SYNTHESIS .1. CONSTRUCTION OF THE CHIRAL BUILDING-BLOCKS FOR ENANTIOSELECTIVE ALKALOID SYNTHESIS VIA AN ASYMMETRIC INTRAMOLECULAR MICHAEL REACTION [J].

HIRAI, Y ;

TERADA, T ;

YAMAZAKI, T ;

MOMOSE, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (04) :509-516

[7] RADICAL CYCLIZATION OF N-(CYCLOHEX-2-ENYL)-ALPHA,ALPHA-DICHLOROACETAMIDES - STEREOSELECTIVE SYNTHESES OF (+/-)-MESEMBRANOL AND (+/-)-ELWESINE [J].

ISHIBASHI, H ;

SO, TS ;

OKOCHI, K ;

SATO, T ;

NAKAMURA, N ;

NAKATANI, H ;

IKEDA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :95-102

[8] THIOHEMIACETAL FORMATION BY INHIBITORY ALDEHYDES AT ACTIVE-SITE OF PAPAIN [J].

LEWIS, CA ;

WOLFENDEN, R .

BIOCHEMISTRY, 1977, 16 (22) :4890-4895

[9]

MARKO IE, 1992, SYNLETT, P275

[10] 3-MEMBERED RINGS .6. POSSIBLE EXPLANATION FOR SOLVENT EFFECT NOTED IN PARTIAL ASYMMETRIC SYNTHESIS OF TRANS-1,2-CYCLOPROPANEDICARBOXYLIC ACID [J].

MCCOY, LL .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (01) :240-&