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Catalytic Electronic Activation: Indirect Addition of Nucleophiles to an Allylic Alcohol
Author(s) -
Black Phillip J.,
Harris William,
Williams Jonathan M. J.
Publication year - 2001
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 - 10.1002/1521-3773(20011203)40:23<4475::aid-anie4475>3.0.co;2-p
Subject(s) - nucleophile , catalysis , alcohol , alkene , ketone , chemistry , allylic alcohol , substrate (aquarium) , nucleophilic addition , medicinal chemistry , allylic rearrangement , photochemistry , organic chemistry , oceanography , geology
Nucleophilic addition to cycloalkenols has been achieved by catalytic electronic activation of the substrate. Catalyzed reversible conversion of the alcohol into a ketone causes electronic activation of the alkene, allowing nucleophilic addition to occur (see scheme).