Synthesis of Chiral 1,4,2-Oxazaphosphorinanes Bearing Pyridyl Substituents

R. G. Zinnatullin^a (https://orcid.org/0000-0002-6516-9232), E. K. Badeeva^a (https://orcid.org/0000-0001-7305-8949), K. A. Nikitina^a (https://orcid.org/0000-0001-5890-1715), K. A. Ivshin^a (https://orcid.org/0000-0002-9720-7977), O. N. Kataeva^a (https://orcid.org/0000-0002-9763-5947), and K. E. Metlushka^a^,* (https://orcid.org/0000-0002-3438-5522)

^aA.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Kazan, 420088 Russia

email: *metlushka@mail.ru

Received 4 October, 2022

Abstract— A series of 1,4,2-oxazaphosphorinanes was synthesized by the three-component reaction of chiral pyridylcontaining imines with trialkyl phosphites and monochloroacetic acid, followed by dealkylation of the P(O)OAlk-fragments of intermediates. It was established that the major diastereomers of the obtained heterocycles have the same configuration at both chiral centers. The synthesized 1,4,2-oxazaphosphorinanes show catalytic activity in the Friedel–Crafts reaction.

Keywords: 1,4,2-oxazaphosphorinanes, chiral 1,2-amino alcohols, imines, phosphonylation, aminophosphonic acids

DOI: 10.1134/S1070363222120118