A New and Convenient Asymmetric Synthesis of α-Amino- and α-Alkyl-α-aminophosphonic Acids Using N-tert-Butylsulfinyl Imines as Chiral Auxiliaries

Qianyi Chen; Chengye Yuan

doi:10.1055/s-2007-990872

PAPER

A New and Convenient Asymmetric Synthesis of α-Amino- and α-Alkyl-α-aminophosphonic Acids Using N-tert-Butylsulfinyl Imines as Chiral Auxiliaries

Qianyi Chen, Chengye Yuan*
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Lingling Lu, Shanghai 200032, P. R. of China
Fax: +86(21)54925379; e-Mail: yuancy@mail.sioc.ac.cn;

Abstract

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Abstract

Nucleophilic addition of dialkyl phosphites to N-tert-butylsulfinyl aldimines or ketimines occurs successfully at room temperature with potassium carbonate as base to afford α-amino- and α-alkyl-α-amino-N-(tert-butylsulfinyl)phosphonates in good to excellent chemical yield and diastereoselectivity. The major diastereomers were separated and smoothly converted into enantiopure α-amino- and α-alkyl-α-aminophosphonic acids.

Key words

α-aminophosphonic acids - α-alkyl-α-aminophosphonic acids - N-tert-butylsulfinyl imines - asymmetric synthesis - nucleophilic addition

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References

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