The first synthesis of cyclic alpha-amino phosphonic acid amides bearing the benzodiazaphosphorinanone system

For the first time, an approach to cyclic alpha-amino phosphonate structure s 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 Pudov ik reaction, starting from the benzodiazaphosphorinanone derivative 1 and s everal sulfur-containing five- and six-membered heterocycles, 2 and 3 (with a reactive C=N double bond) as imine component (yields up to 81%). Further more, the diastereoselectivity of the reaction was investigated (dr up to 6 2:38). (C) 1998 John Wiley & Sons, Inc.