An eco-friendly N-benzoylglycine/thiourea cooperative catalyzed stereoselective synthesis of β-L-rhamnopyranosides

Abstract

A new practical utility for β-stereoselective L-rhamnopyranosylations are conducted using rhamnosyl trichloroacetimidate donors in the presence of N-benzoylglycine/thiourea cooperative catalysis. This method represents the first instance where amino acid derivative N-benzoylglycine is used as a catalyst for β-L-rhamnopyranosylations. This method represents the first instance where environmentally benign amino acid derivative, such as N-benzoylglycine which is reported as less toxic and can be used as efficient catalyst for smooth transformation under eco friendly conditions.On the other hand β-stereoselectivity of rhamnosyl trichloroacetimidate donors protected with O-picoloyl groups at remote positions (C-2 and C-3) has been investigated while the glycosylation reactions of 2-O-picoloyl group substituted l-rhamnosyl donor displays predominant β-stereoselectivity. Reaction proceeded smoothly with moderate to high yield under mild reaction conditions at room temperature with 10 mol% catalyst loadings and tolerant of a wide range of glycoside acceptors.