Asymmetric Hydrophosphylation of Chiral N-Phosphonyl Imines Provides an Efficient Approach to Chiral alpha-Amino Phosphonates

作者：Kaur Parminder; Wever Walter; Rajale Trideep; Li Guigen^*

来源：Chemical Biology & Drug Design, 2010, 76(4): 314-319.

DOI：10.1111/j.1747-0285.2010.01013.x

• N-phosphonyl imine
• chiral alpha-amino phosphonates

Chiral N-phosphonylimines were found to react with lithium phosphites to provide various substituted chiral alpha-amino phosphonates in excellent yields (94-97%) and diastereoselectivities (93:7-99:1). The types of bases utilized for generating the nucleophile are crucial for the effectiveness of asymmetric induction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxilliary was proven to be superior to other protecting groups in controlling diastereoselectivity. The absolute configuration was unambiguously determined by converting a chiral alpha-amino phosphonate into its authentic N-Cbz derivative.

• 出版日期2010-10