[2+2] CYCLOADDITION REACTION OF CYCLIC ENECARBAMATES AND ENAMIDES WITH KETENES - A SHORT AND EFFICIENT SYNTHESIS OF THE GEISSMAN-WAISS LACTONE

被引：29

作者：

DEFARIA, AR ^{[1
]}

MATOS, CRR ^{[1
]}

CORREIA, CRD ^{[1
]}

机构：

[1] UNIV FED RIO DE JANEIRO,CTR CIENCIAS SAUDE,B1H,BR-21941 RIO JANEIRO,BRAZIL

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)60049-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of several 2-aza-bicyclo[3.2.0]heptan-6-ones has been achieved in a regiospecific manner through a [2+2] cycloaddition reaction between five-membered cyclic enecarbamates and enamides and free ketenes. The synthetic potential of this new methodology has been demonstrated by a concise synthesis of the Geissman-Waiss lactone in 62% overall yield.

引用

页码：27 / 30

页数：4

共 17 条

[1] CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS [J].

BELLUS, D ;

ERNST, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :797-827

[2]

BRADY WT, 1981, TETRAHEDRON, V37, P1948

[3] ENATIOSPECIFIC SYNTHESIS OF (+)-RETRONECINE, (+)-CROTONECINE, AND RELATED ALKALOIDS [J].

BUCHANAN, JG ;

JIGAJINNI, VB ;

SINGH, G ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2377-2384

[4]

CAMPBELL AL, 1987, SYNTHESIS-STUTTGART, P421

[5]

DEFARIA AR, 1992, THESIS

[6] TOTAL SYNTHESIS OF (+)-RETRONECINE [J].

GEISSMAN, TA ;

WAISS, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :139-&

[7]

GHOSEZ L, 1977, PERICYCLIC REACTIONS, V2, P79

[8] SYNTHESIS OF OPTICALLY-ACTIVE CYCLOBUTANONES BY THE PHOTOLYSIS OF CHROMIUM ALKOXYCARBENE COMPLEXES IN THE PRESENCE OF OPTICALLY-ACTIVE ENE CARBAMATES [J].

HEGEDUS, LS ;

BATES, RW ;

SODERBERG, BC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :923-927

[9] A FACILE SYNTHESIS OF N-ACYL-2-PYRROLINES [J].

KRAUS, GA ;

NEUENSCHWANDER, K .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4791-4792

[10]

LENZ GR, 1978, SYNTHESIS-STUTTGART, P489

← 1 2 →