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anti ‐Selective Asymmetric Synthesis of β‐Hydroxy‐α‐amino Acid Esters by the in situ Generated Chiral Quaternary Ammonium Fluoride‐Catalyzed Mukaiyama‐Type Aldol Reaction
Author(s) -
Ooi Takashi,
Taniguchi Mika,
Doda Kanae,
Maruoka Keiji
Publication year - 2004
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.200404111
Subject(s) - chemistry , ketene , aldol reaction , catalysis , acetal , ammonium , in situ , enantioselective synthesis , silylation , organic chemistry , fluoride , medicinal chemistry , inorganic chemistry
The aldol coupling of ketene silyl acetal 2 derived from the glycinate Schiff base with aldehydes can be efficiently catalyzed by an in situ generated, chiral quaternary ammonium fluoride of type 1 under mild, neutral conditions, affording the corresponding anti ‐β‐hydroxy‐α‐amino esters predominantly with excellent enantioselectivities.