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Unexpected cis‐ Selective 1,4‐Addition Reaction of Lower Order Cyanocuprates to Optically Active 5 ‐ ( tert‐ Butyldimethylsiloxy)‐2‐cyclohexenone
Author(s) -
HareauVittini Georges,
Hikichi Shinichi,
Sato Fumie
Publication year - 1998
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/(sici)1521-3773(19980817)37:15<2099::aid-anie2099>3.0.co;2-u
Subject(s) - enantiomer , optically active , selectivity , cyclohexenone , chemistry , order (exchange) , alkyl , stereochemistry , organic chemistry , catalysis , finance , economics
A remarkable cis selectivity has been observed in the 1,4‐addition of lower order primary and secondary alkylcyanocuprates to 5‐silyloxy‐ and 5‐benzyloxy‐substituted cyclohexenones. This enables the preparation of both enantiomers of the corresponding 5‐alkyl‐substituted cyclohexenones ( S )‐ and ( R )‐ 3 by the reaction of the readily available 5‐( tert‐ butyldimethylsiloxy)‐2‐cyclohexenone ( 1 ) with either the lower or higher order cyanocuprate. DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene.