Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates.
A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.
Fandrick
Keith R
KR
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. keith.fandrick@boehringer-ingelheim.com
Fandrick
Daniel R
DR
Gao
Joe J
JJ
Reeves
Jonathan T
JT
Tan
Zhulin
Z
Li
Wenjie
W
Song
Jinhua J
JJ
Lu
Bruce
B
Yee
Nathan K
NK
Senanayake
Chris H
CH
D000498:Allyl Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D015032:Zinc / Q000737:chemistry*
D000498:Allyl Compounds; D001896:Boron Compounds; D007659:Ketones; D015032:Zinc