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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.