The first synthesis of cyclic α‐amino phosphonic acid amides bearing the benzodiazaphosphorinanone system

Abstract

For the first time, an approach to cyclic α-amino phosphonate structures bearing a 5,6-benzo[1,3,2]diazaphosphorinan-4-one 2-oxide framework is described. The desired products, 4 and 5, were prepared by a modified Pudovik reaction, starting from the benzodiazaphosphorinanone derivative 1 and several sulfur-containing five- and six-membered heterocycles, 2, and 3 (with a reactive C=N double bond) as imine component (yields up to 81%). Furthermore, the diastereoselectivity of the reaction was investigated (dr up to 62:38). © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9: 679–686, 1998