Chiral N-phosphonyl imine chemistry: An efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

Parminder Kaur, Gaurav Shakya, Hao Sun, Yi Pan, Guigen Li

Research output: Contribution to journalArticle

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Abstract

A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96:4 to 99:1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.

Original languageEnglish
Pages (from-to)1091-1096
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number5
DOIs
StatePublished - 2010

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