Convenient Synthesis of 4-Methylene-2-oxazolidinones and 4-Methylenetetrahydro-1, 3-oxazin-2-ones via Transition-Metal Catalyzed Intramolecular Addition of …

Y Tamaru, M Kimura, S Tanaka, S Kure…

Index: Tamaru; Kimura; Tanaka; Kure; Yoshida Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 10 p. 2838 - 2849

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Citation Number: 41

Abstract

2-Propynyl tosylcarbamates 1 undergo cyclization smoothly by the catalysis of CuCl/Et 3 N or AgNCO/Et 3 N to furnish 4-methylene-2-oxazolidinones 2 in good yields. The similar cyclization of the N-acyl derivatives of 1 (PhCO, MeCO, EtOCO, etc.) is catalyzed effectively by AgNCO/t-BuOK. These reactions accommodate a variety of substituents at C 1 and C 3 of 2-propyn-1-ol and provide (Z)-2 as single stereoisomers. The scope of the cyclization of 3- ...