Copper‐Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons | Zendy

Welle Alexandre | Zendy; Petrignet Julien | Zendy; Tinant Bernard | Zendy; Wouters Johan | Zendy; Riant Olivier | Zendy

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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.

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