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■ A Novel Synthesis of 1,2-Dehydro-1-aminophosphonates via Beckmann Rearrangement. Application to the Synthesis of a-Aminophosphonic Acid Derivatives

Tsutomu Yokomatsu, Takayuki Minowa, Yoshinori Yoshida, and Shiroshi Shibuya*

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Beckmann rearrangement of oxime mesylates (6a,b and 6d) mediated by TiCl₄, in the presence of (EtO)₃P gave the 1,2-dehydro-1-aminophosphonates (7a,b and 7d) in good yield. The utility of 7a,b was illustrated by a synthesis of α-aminophosphonates (11) and (12).