Enantioselective Formation of Stereogenic Carbon–Fluorine Centers by a Simple Catalytic Method | Zendy

Marigo Mauro | Zendy; Fielenbach Doris | Zendy; Braunton Alan | Zendy; Kjærsgaard Anne | Zendy; Jørgensen Karl Anker | Zendy

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Enantioselective Formation of Stereogenic Carbon–Fluorine Centers by a Simple Catalytic Method

Author(s) -

Marigo Mauro,

Fielenbach Doris,

Braunton Alan,

Kjærsgaard Anne,

Jørgensen Karl Anker

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.200500395

Subject(s) - stereocenter , enantioselective synthesis , steric effects , fluorine , catalysis , enantiomer , carbon fibers , chemistry , organic chemistry , stereochemistry , combinatorial chemistry , computer science , algorithm , composite number

An easy protocol has been developed for the formation of stereogenic carbon–fluorine centers by the organocatalytic asymmetric α‐fluorination of aldehydes 1 . The 2‐fluoroaldehydes 4 are formed with 2 as the fluorinating agent and only 1 mol % of a sterically demanding silylated prolinol 3 as catalyst. The 2‐fluoroaldehydes are subsequently reduced to the corresponding alcohols 5 without loss of enantiomeric excess.

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