Download PDF
Synlett 1992; 1992(10): 817-820
DOI: 10.1055/s-1992-21503
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

(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).