Chiral N-phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α-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 α-amino phosphonate into its authentic N-Cbz derivative.
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Kaur et al. (2010) studied this question.
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