Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Org Biomol Chem. 2010 Mar 7;8(5):1091-6. doi: 10.1039/b923914f. Epub 2010 Jan 5.
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.
通过手性 N-磷酰亚胺与芳基/烷基锂炔反应，合成了各种取代的手性炔丙胺。研究了 17 个实例，产率很高（>90%），非对映选择性也很好（96:4 至 99:1）。结果表明，生成炔的碱的类型和溶剂对不对称反应的效率至关重要。此外，手性 N-磷酰亚胺助剂上的 N,N-异丙基取代基在控制非对映选择性方面优于其他保护基。
