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.
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.
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