A THERMODYNAMIC PREFERENCE OF CHIRAL N-METHANESULFONYL AND N-ARENESULFONYL 2,3-CIS-3-ALKYL-2-VINYLAZIRIDINES OVER THEIR 2,3-TRANS-ISOMERS -USEFUL PALLADIUM(0)-CATALYZED EQUILIBRATION REACTIONS FOR THE SYNTHESIS OF (E)-ALKENE DIPEPTIDE ISOSTERES

Authors
IBUKA T MIMURA N AOYAMA H AKAJI M OHNO H MIWA Y TAGA T NAKAI K TAMAMURA H FUJII N YAMAMOTO Y
Citation
T. Ibuka et al., A THERMODYNAMIC PREFERENCE OF CHIRAL N-METHANESULFONYL AND N-ARENESULFONYL 2,3-CIS-3-ALKYL-2-VINYLAZIRIDINES OVER THEIR 2,3-TRANS-ISOMERS -USEFUL PALLADIUM(0)-CATALYZED EQUILIBRATION REACTIONS FOR THE SYNTHESIS OF (E)-ALKENE DIPEPTIDE ISOSTERES, Journal of organic chemistry, 62(4), 1997, pp. 999-1015
Citations number
128
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
4
Year of publication
1997
Pages
999 - 1015
Database
ISI
SICI code
0022-3263(1997)62:4<999:ATPOCN>2.0.ZU;2-U
Abstract
Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulf onyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more s table than the corresponding 2,3-trans-isomers in accord with ab initi o calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-i sobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.