N-phosphinoylimines: An emerging class of reactive intermediates for stereoselective organic synthesis

Steven M. Weinreb, Robert K. Orr

Research output: Contribution to journalReview articlepeer-review

113 Scopus citations


N-Phosphinoylimines have recently begun to attract significant attention from synthetic chemists for the preparation of nitrogen-containing molecules. Several methods have been developed for the synthesis, or in situ generation, of these reactive electrophilic species. N-Phosphinoylimines undergo a wide range of reactions, including nucleophilic additions and cycloadditions. These imines are also effective electrophiles in a number of diastereoselective and enantioselective reactions. An advantage of using N-phosphinoylimines is that the reaction products can be easily deprotected under mild acidic conditions, leading to amines. This review outlines the preparation and uses of N-phosphinoylimines with particular emphasis on their applications in stereoselective processes. copy; Georg Thieme Verlag Stuttgart.

Original languageEnglish (US)
Pages (from-to)1205-1227
Number of pages23
Issue number8
StatePublished - May 20 2005

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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