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 language | English |
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Pages (from-to) | 1091-1096 |
Number of pages | 6 |
Journal | Organic and Biomolecular Chemistry |
Volume | 8 |
Issue number | 5 |
DOIs | |
State | Published - 2010 |