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

被引：19

作者：

Kaur, Parminder ^{[1
]}

Wever, Walter ^{[1
]}

Rajale, Trideep ^{[1
]}

Li, Guigen ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

CHEMICAL BIOLOGY & DRUG DESIGN | 2010年 / 76卷 / 04期

关键词：

N-phosphonyl imine; chiral alpha-amino phosphonates; ENANTIOSELECTIVE HYDROPHOSPHONYLATION; CHEMISTRY; INHIBITION; ALDEHYDES; PHOSPHONOPEPTIDES; ADDITIONS; ALANINE; ACIDS;

D O I：

10.1111/j.1747-0285.2010.01013.x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：314 / 319

页数：6

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