Enantioselective Biocatalytic Oxidative Desymmetrization of Substituted Pyrrolidines | Zendy

Köhler Valentin | Zendy; Bailey Kevin R. | Zendy; Znabet Anass | Zendy; Raftery James | Zendy; Helliwell Madeleine | Zendy; Turner Nicholas J. | Zendy

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Enantioselective Biocatalytic Oxidative Desymmetrization of Substituted Pyrrolidines

Author(s) -

Köhler Valentin,

Bailey Kevin R.,

Znabet Anass,

Raftery James,

Helliwell Madeleine,

Turner Nicholas J.

Publication year - 2010

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.200906655

Subject(s) - enantioselective synthesis , chemistry , desymmetrization , enantiomer , aspergillus niger , organic chemistry , catalysis , enantiomeric excess , combinatorial chemistry , biochemistry

Made up out of air : The highly enantioselective oxidation of 3,4‐substituted meso ‐pyrrolidines to Δ 1 ‐pyrrolines is reported. The reaction is catalyzed by monoamine oxidase from Aspergillus niger (MAO‐N D5) and utilizes molecular oxygen from air as the stoichiometric oxidant. The corresponding Δ 1 ‐pyrrolines serve as useful building blocks for the synthesis of L ‐proline analogues and α‐amino nitriles of high enantiomeric purity.

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