A new and convenient asymmetric synthesis of α-amino- and α-alkyl-α-aminophosphonic acids using N-tert-butylsulfinyl imines as chiral auxiliaries

被引：33
|
作者：
Chen, Qianyi [1 ]
Yuan, Chengye [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2007年 / 24期
关键词：
alpha-aminophosphonic acids; alpha-alkyl-alpha-aminophosphonic acids; N-tert-butylsulfinyl imines; asymmetric synthesis; nucleophilic addition;
D O I：
10.1055/s-2007-990872
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nucleophilic addition of dialkyl phosphites to N-tert-butylsulfinyl aldimines or ketimines occurs successfully at room temperature with potassium carbonate as base to afford alpha-amino- and alpha-alkyl-alpha-amino-N-(tert-butylsulfinyl)phosphonates in good to excellent chemical yield and diastereoselectivity. The major diastereomers were separated and smoothly converted into enantiopure alpha-amino- and alpha-alkyl-alpha-aminophosphonic acids.
引用
收藏
页码：3779 / 3786
页数：8
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