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

✍ Scribed by Harald Gröger; Jörg Wilken; Jürgen Martens; Ion Neda; Reinhard Schmutzler

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
197 KB
Volume
9
Category
Article
ISSN
1042-7163

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✦ Synopsis

For the first time, an approach to cyclic ␣-amino phosphonate structures bearing a 5, 6benzo[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 C‫ס‬N double bond) as imine component (yields up to 81%). Furthermore, the diastereoselectivity of the reaction was investigated (dr up to 62:38).

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