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Glycosylation‐Induced and Lewis Acid‐Catalyzed Asymmetric Synthesis of β‐ N ‐Glycosidically Linked α‐Aminophosphonic Acids Derivatives
Author(s) -
Wang Yadan,
Wang Fei,
Wang Yangyun,
Miao Zhiwei,
Chen Ruyu
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800406
Subject(s) - chemistry , boron trifluoride , diastereomer , catalysis , lewis acids and bases , mannich reaction , yield (engineering) , boron , glycosylation , organic chemistry , lewis acid catalysis , medicinal chemistry , biochemistry , materials science , metallurgy
The diastereospecific formation of β‐ N ‐glycosidically linked α‐aminophosphonic acids derivatives has been achieved with high yield via a Mannich‐type reaction. The reaction was performed by using O ‐pivaloylated galactosylamine 1 as a chiral template and boron trifluoride diethyl etherate as a catalyst in THF. Imines 3 of aromatic compounds and diethyl phosphite were converted to N ‐galactosyl α‐aminoalkylphosphonate 4 , giving ratios of diastereomers higher than 19:1. This procedure provides a rapid access to biologically important galactosyl α‐aminophosphonic acids derivatives.