Abstract
Five olefins, each possessing an aryl (Ar) group, an aliphatic moiety, and a protected amino group as N-Teoc (-CO 2 (CH 2 ) 2 TMS) or N 3 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.
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