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A 100 Gram‐Scale Production of a Key Building Block of Antibacterial Vancomycin: The Use of an Air‐Stable Chiral Zirconium Catalyst and Complete Recovery of a Silicon Source in Catalytic Asymmetric Mukaiyama Aldol Reaction
Author(s) -
Isoda Takeshi,
Akiyama Ryo,
Oyamada Hidekazu,
Kobayashi Shū
Publication year - 2006
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.200606182
Subject(s) - chemistry , catalysis , zirconium , aldol reaction , yield (engineering) , enantioselective synthesis , silicon , gram , molecular sieve , combinatorial chemistry , organic chemistry , bacteria , materials science , biology , metallurgy , genetics
We have achieved a 100 gram‐scale production of anti ‐(2 S ,3 S )‐β‐( p ‐benzyloxy‐ m ‐chloro)phenyl‐ N ‐trifluoroacetyl‐ L ‐serine methyl ester ( 1 ) in high yield with high diastereo‐ and enantioselectivities based on a catalytic asymmetric Mukaiyama aldol reaction. The use of an air‐stable zirconium‐molecular sieves combined catalyst [( R )‐I 4 ‐ZrMS] facilitates easy manufacturing operation and reproducibility. Moreover, this is the first example of the complete recovery of the silicon source in a Mukaiyama aldol reaction.