PALLADIUM-CATALYZED REDUCTIVE RING-OPENING WITH FORMIC-ACID OF AZIRIDINES BEARING AN ALPHA,BETA-UNSATURATED ESTER GROUP

Authors
OHNO H MIMURA N OTAKA A TAMAMURA H FUJII N IBUKA T SHIMIZU I SATAKE A YAMAMOTO Y
Citation
H. Ohno et al., PALLADIUM-CATALYZED REDUCTIVE RING-OPENING WITH FORMIC-ACID OF AZIRIDINES BEARING AN ALPHA,BETA-UNSATURATED ESTER GROUP, Tetrahedron, 53(38), 1997, pp. 12933-12946
Citations number
49
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
38
Year of publication
1997
Pages
12933 - 12946
Database
ISI
SICI code
0040-4020(1997)53:38<12933:PRRWFO>2.0.ZU;2-X
Abstract
The palladium-catalyzed reduction of various N-arenesulfonylaziridines bearing alpha,beta-unsaturated ester groups with formic acid and the stereochemistry of the reaction products have been investigated in det ail. In all cases examined, (Z)-alpha,beta-enoates, (E)-alpha,beta-eno ates, and (E)-beta,gamma-enoates bearing amino functionality at the de lta-position were obtained. The formation of these three reduction pro ducts was taken as an indication that palladium-catalyzed isomerizatio n occurs prior to the reduction step. (C) 1997 Elsevier Science Ltd.