PALLADIUM-TEMPLATED REGIOSELECTIVE AND STEREOSELECTIVE CYCLIZATION OF2'-ALKENYL 2-ALKYNOATES AND ITS SYNTHETIC APPLICATIONS

Authors
JI JG ZHANG CM LU XY
Citation
Jg. Ji et al., PALLADIUM-TEMPLATED REGIOSELECTIVE AND STEREOSELECTIVE CYCLIZATION OF2'-ALKENYL 2-ALKYNOATES AND ITS SYNTHETIC APPLICATIONS, Journal of organic chemistry, 60(5), 1995, pp. 1160-1169
Citations number
80
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
5
Year of publication
1995
Pages
1160 - 1169
Database
ISI
SICI code
0022-3263(1995)60:5<1160:PRASCO>2.0.ZU;2-U
Abstract
2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a cata lytic amount of palladium complex in the presence of CuX(2) and LiX. W hen an alkyl group is introduced to the 1'-position of the alkenyl gro up, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubsti tuted gamma-lactones, and substituted 2-propynoates afford cis-beta,ga mma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.