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Copper‐Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons
Author(s) -
Welle Alexandre,
Petrignet Julien,
Tinant Bernard,
Wouters Johan,
Riant Olivier
Publication year - 2010
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.201000907
Subject(s) - aldol reaction , domino , quaternary carbon , chemistry , copper , silylation , cascade reaction , catalysis , organic chemistry , medicinal chemistry , enantioselective synthesis
Asymmetric aldol reaction : A domino silylation–aldol reaction between enoyloxazolidinones and various aldehydes has been developed (see scheme). The process catalysed by a copper complex in the presence of a borosilane led to high diastereoselectivities. Yields between 59 and 90 % and d.r. values between 78:22 to 95:5 were obtained. When methacryloyloxazolidinones were used, a controlled chiral quaternary carbon was generated. BPin=4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl.