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Synlett 1992; 1992(10): 817-820
DOI: 10.1055/s-1992-21503
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Retention of Configuration in Displacement Reactions of 2-Chloro-1,3,2-oxazaphospholidin-2-one. Stereoselective 1,4-Addition Reaction of the Anion of Chiral 2-Propenylphosphonamide

Duy H. Hua* , Jin Shan Chen, Shankar Saha, Hui Wang, Didier Roche, S. Narasimha Bharathi, Roch Chan-Yu-King, Paul D. Robinson, Sadahiko Iguchi
  • *Department of Chemistry, Kansas State University Manhattan, Kansas 66506, USA
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Publication History

Publication Date:
08 March 2002 (online)

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(2S,4R,5R)-3-Isopropyl-4-methyl-5-phenyl-2-(2-propenyl)-1,3, 2-oxazaphospholidin-2-one (1) was synthesized stereospecifically from (2R,4R,5R)-2-chloro-3-isopropyl-4-methyl-5-phenyl-1,3, 2-oxazaphospholidin-2-one (5) with allylmagnesium bromide or the diallylaluminum reagent, and its structure was verified by a single crystal X-ray analysis. The anion of 1 underwent exclusive stereoselective 1, 4-addition reaction with ethyl 3,4-dihydro-4-oxo-(2H)-pyridine-1-carboxylate (7).

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