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
The Journal of Organic Chemistry1997Vol. 62(4), pp. 999–1015
Citations Over TimeTop 1% of 1997 papers
Toshiro Ibuka, Norio Mimura, Hiroshi Aoyama, Masako Akaji, Hiroaki Ohno, Yoshihisa Miwa, Tooru Taga, Kazuo Nakai, Hirokazu Tamamura, Nobutaka Fujii, Yoshinori Yamamoto
Abstract
Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.
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