79345-26-9Relevant academic research and scientific papers
A Highly Regioselective Reaction of Allylic Acetates with Silylated Carbon Nucleophiles Directed by a Sulfenyl Group. Scope, Limitation, and Mechanistic Aspects
Kudo, Kazuaki,Hashimoto, Yukihiko,Houchigai, Hitoshi,Hasegawa, Masaki,Saigo, Kazuhiko
, p. 848 - 856 (2007/10/02)
α-(Sulfenylmethyl)allyl acetates reacted with silylated carbon nucleophiles in the presence of a catalytic amount of TMSOTf to give products substituted at the α-position of the sulfenylmethyl group in moderate to good yields with high regioselectivity.The theoretical calculation on an intermediate cationic species indicated that an episulfonium ion was a stable form; the observed regioselectivity was rationalized qualitatively on the basis of the coefficients of LUMO of the cation.Some transformations of the products were also demonstrated.
