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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).