Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an alpha,beta-Unsaturated Ester Group: A Thermodynamic Preference for Chiral Alkyl (2E)-4,5-cis-4,5-Epimino-N-(alkyl- or arylsulfonyl) 2-Enoates over the Other Three Stereoisomers

Toshiro Ibuka; Norio Mimura; Hiroaki Ohno; Kazuo Nakai; Masako Akaji; Hiromu Habashita; Hirokazu Tamamura; Yoshihisa Miwa; Tooru Taga; Nobutaka Fujii; Yoshinori Yamamoto

doi:10.1021/jo962094u

Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an alpha,beta-Unsaturated Ester Group: A Thermodynamic Preference for Chiral Alkyl (2E)-4,5-cis-4,5-Epimino-N-(alkyl- or arylsulfonyl) 2-Enoates over the Other Three Stereoisomers

J Org Chem. 1997 May 2;62(9):2982-2991. doi: 10.1021/jo962094u.

Authors

Toshiro Ibuka¹, Norio Mimura, Hiroaki Ohno, Kazuo Nakai, Masako Akaji, Hiromu Habashita, Hirokazu Tamamura, Yoshihisa Miwa, Tooru Taga, Nobutaka Fujii, Yoshinori Yamamoto

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980, Japan.

PMID: 11671663
DOI: 10.1021/jo962094u

Abstract

Palladium(0)-catalyzed reactions of five sets of four stereoisomeric 4,5-epimino-N-(methanesulfonyl) or -N-(arylsulfonyl) 2-enoates reveal that 4,5-cis-(2E)-isomers are thermodynamically more stable than other isomers, in accord with calculations. A highly stereoselective synthesis of (E)-alkene dipeptide isosteres having the desired stereochemistries from unwanted stereoisomeric 4,5-epimino-N-(arylsulfonyl) 2-enoates is also presented.