手性 N-膦酰亚胺的不对称氢膦化反应为手性 α-氨基膦酸酯提供了一种有效的合成方法。
Asymmetric hydrophosphylation of chiral N-phosphonyl imines provides an efficient approach to chiral α-amino phosphonates.
机构信息
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
出版信息
Chem Biol Drug Des. 2010 Oct;76(4):314-9. doi: 10.1111/j.1747-0285.2010.01013.x.
Abstract
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.
摘要
手性 N-膦酰亚胺与亚磷酸锂反应，以优异的收率（94-97%）和非对映选择性（93:7-99:1）得到各种取代的手性α-氨基膦酸酯。用于生成亲核试剂的碱的类型对于不对称诱导的有效性至关重要。此外，手性 N-膦酰亚胺辅助剂上的 N，N-异丙基被证明优于其他保护基，可更好地控制非对映选择性。通过将手性α-氨基膦酸酯转化为其真实的 N-Cbz 衍生物，可明确确定绝对构型。
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