SYNTHESIS OF A SERIES OF STRUCTURAL ANALOGUES OF THE CINCHONA ALKALOIDS

摘要

Five olefins,each possessing an aryl (Ar) group,an aliphatic moiety,and a protected amino group as N-Teoc (-CO2(CH2)2TMS) or N3 at the aliphatic end,were converted to the corresponding epoxides with high ee.The amino group was generated by deprotection of the N-Teoc group with CsF or by Staudinger reaction of the azide group at elevated temperatures,under which the intramolecular epoxide ring-opening with the resulting amino group took place concomitantly to afford the analogues of the Cinchona alkaloids.