Silver (I)-Catalyzed Aminocyclization of 2, 3-Butadienyl and 3, 4-Pentadienyl Carbamates: An Efficient and Stereoselective Synthesis of 4-Vinyl-2-oxazolidionones and …

M Kimura, S Tanaka, Y Tamaru

Index: Kimura; Tanaka; Tamaru Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 6 p. 1689 - 1705

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Citation Number: 33

Abstract

Silver (I) salts in combination with an appropriate base (mostly triethylamine) catalyzed the aminocyclization of N-substituted 2, 3-butadienyl carbamates 1 (benzene, 50° C) to provide 4-vinyl-2-oxazolidinones 2 in good yields. The stereoselectivity (trans-2/cis-2) ranged from 1.4 for C 5-Me to> 30 for C 5-phenyl, isopropenyl, and t-butyl derivatives. 3, 4-Pentadienyl tosylcarbamates 3, the one-carbon higher homologues of 1, underwent a similar ...