The asymmetric catalytic aldol reaction of allenolates with aldehydes using n-fluoroacyl oxazaborolidine as the catalyst.
The asymmetric catalytic aldol reaction of silyl allenolates with aldehydes has been achieved by using N-C(3)F(7)CO oxazaborolidine as the catalyst. The fluoroacyl group of the catalyst was found to be crucial for control of enantioselectivity. The reaction provides the first enantioselective approach to beta-halo Baylis-Hillman-type adducts.
Li
G
G
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA. qeggl@ttu.edu
Wei
H X
HX
Phelps
B S
BS
Purkiss
D W
DW
Kim
S H
SH
D000447:Aldehydes / Q000737:chemistry*; D001896:Boron Compounds; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000447:Aldehydes; D001896:Boron Compounds; D007202:Indicators and Reagents; D009281:Naphthalenes; C426407:n-fluoroacyl oxazaborolidine; C116609:3-hydroxybutanal; C110055:allenolic acid