Highly Enantioselective Preparation of Tertiary Alcohols and Amines by Copper‐Mediated Diastereoselective Allylic S N 2′ Substitutions | Zendy

Leuser Helena | Zendy; Perrone Sylvie | Zendy; Liron Frédéric | Zendy; Kneisel Florian F. | Zendy; Knochel Paul | Zendy

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Highly Enantioselective Preparation of Tertiary Alcohols and Amines by Copper‐Mediated Diastereoselective Allylic S N 2′ Substitutions

Author(s) -

Leuser Helena,

Perrone Sylvie,

Liron Frédéric,

Kneisel Florian F.,

Knochel Paul

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200500672

Subject(s) - allylic rearrangement , enantioselective synthesis , ozonolysis , chemistry , reagent , hydroboration , sequence (biology) , organic chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , catalysis , biochemistry

Trisubstituted allylic pentafluorobenzoates react with diorganozinc reagents in the presence of CuCN⋅2 LiCl to provide alkenes bearing a chiral quaternary center in α position (>95 % ee ). These alkenes are readily converted into chiral tertiary alcohols or into chiral amino alcohols by a straightforward sequence of ozonolysis followed by Curtius rearrangement (see scheme).

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