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 |
|---|---|
| Pages (from-to) | 1091-1096 |
| Number of pages | 6 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 8 |
| Issue number | 5 |
| DOIs | |
| State | Published - 2010 |
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Kaur, P., Shakya, G., Sun, H., Pan, Y., & Li, G. (2010). Chiral N-phosphonyl imine chemistry: An efficient asymmetric synthesis of chiral N-phosphonyl propargylamines. Organic and Biomolecular Chemistry, 8(5), 1091-1096. https://doi.org/10.1039/b923914f