92208-94-1Relevant articles and documents
Asymmetric Synthesis of 2-Organo-1,3,2-oxazaphospholidines
Richter, Wolf Juergen
, p. 2328 - 2336 (2007/10/02)
Achiral organophosphonous diamides RP(NMe2)2 react with chiral amino alcohols such as L-ephedrine and L-prolinol to form methyl- and phenyl-substituted mono- (2,3) and bicyclic 1,3,2-oxazaphospholidines (6-8) in good yields.Organophosphonous dichloride allow the synthesis of oxazaphospholidines only for R = tert-butyl (4,5).The diastereomeric excess of the ephedrine and prolinol derivatives ranges from 80percent (R = methyl) to 95percent d.e. (R = tert-butyl).The bis-1,3,2-oxazaphospholidine 8, made from two mols of prolinol and one mol of 1,2-ethanediylbis, is virtually diastereomerically pure according to the NMR spectrum.Analysis of the 13C-31P and 1H-31P coupling constants afford the structural assignment of the ephedrine derivatives as (2S,4S,5R) and the prolinol derivatives as (2R,5S).