NOVEL ASYMMETRIC PHENYLSELENIUM-INDUCED LACTAMIZATIONS OF OLEFINIC AMIDES - STEREOSELECTIVE ROUTES TO ALPHA-AMINO AND BETA-AMINO ACIDS

Organoselenium-induced cyclofunctionalization of the (S)-N-(alpha,beta -unsaturated) acylprolinamides 1, 7 and 14 has been found to produce t he 7-membered bislactam products 2 and 15, or the 6-membered phenylsel enolactam products 8 and 9 depending on the substitution pattern of th e enone moiety of the starting material. The structural identities and stereochemistry of the cyclized products have been determined by X-ra y diffraction, and the diastereoselectivity in the formation of the 7- membered ring bislactam product was found to be 91.6% de. The mechanis m of the cyclolactamization is discussed.