Stereoselective Synthesis of α‐Amino(phenyl)methyl(phenyl)phosphinic Acids with  O ‐Pivaloylated  D ‐Galactosylamine as Chiral Auxiliary | Zendy

Wang Yadan | Zendy; Wang Yangyun | Zendy; Yu Jipan | Zendy; Miao Zhiwei | Zendy; Chen Ruyu | Zendy

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Stereoselective Synthesis of α‐Amino(phenyl)methyl(phenyl)phosphinic Acids with O ‐Pivaloylated D ‐Galactosylamine as Chiral Auxiliary

Author(s) -

Wang Yadan,

Wang Yangyun,

Yu Jipan,

Miao Zhiwei,

Chen Ruyu

Publication year - 2009

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200901419

Subject(s) - stereoselectivity , chemistry , yield (engineering) , mannich reaction , chiral auxiliary , stereochemistry , glycoside , amino acid , enantioselective synthesis , organic chemistry , catalysis , materials science , biochemistry , metallurgy

The diastereospecific formation of β‐ N ‐glycoside‐linked α‐amino phosphonic acid derivatives has been achieved in high yield by a Mannich‐type reaction. The reaction was performed by using O ‐pivaloylated galactosylamine as a chiral template and SnCl 4 as a promoter in THF (see scheme).

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