PALLADIUM(0)-CATALYZED ISOMERIZATION-REACTIONS OF AZIRIDINES BEARING AN ALPHA,BETA-UNSATURATED ESTER GROUP - A THERMODYNAMIC PREFERENCE FORCHIRAL ALKYL (2E)-4,5-CIS-4,5-EPIMINO-N-(ALKYL-SULFONYL OR ARYLSULFONYL) 2-ENOATES OVER THE OTHER 3 STEREOISOMERS

Authors
IBUKA T MIMURA N OHNO H NAKAI K AKAJI M HABASHITA H TAMAMURA H MIWA Y TAGA T FUJII N YAMAMOTO Y
Citation
T. Ibuka et al., PALLADIUM(0)-CATALYZED ISOMERIZATION-REACTIONS OF AZIRIDINES BEARING AN ALPHA,BETA-UNSATURATED ESTER GROUP - A THERMODYNAMIC PREFERENCE FORCHIRAL ALKYL (2E)-4,5-CIS-4,5-EPIMINO-N-(ALKYL-SULFONYL OR ARYLSULFONYL) 2-ENOATES OVER THE OTHER 3 STEREOISOMERS, Journal of organic chemistry, 62(9), 1997, pp. 2982-2991
Citations number
54
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
9
Year of publication
1997
Pages
2982 - 2991
Database
ISI
SICI code
0022-3263(1997)62:9<2982:PIOABA>2.0.ZU;2-R
Abstract
Palladium(0)-catalyzed reactions of five sets of four stereoisomeric 4 ,5-epimino-N-(methanesulfonyl) or -N-(arylsulfonyl) 2-enoates reveal t hat 4,5-cis-(2E)-isomers are thermodynamically more stable than other isomers, in accord with calculations. A highly stereoselective synthes is of (E)-alkene dipeptide isosteres having the desired stereochemistr ies from unwanted stereoisomeric 4,5-epimino-N-(arylsulfonyl) 2-enoate s is also presented.