Concatenated catalytic asymmetric allene diboration/allylation/functionalization.
[reaction: see text] Palladium-catalyzed enantioselective diboration of prochiral allenes generates a reactive chiral allylboron intermediate which is a versatile reagent for the allylation of carbonyls. Experiments that improve the enantioselectivity of this process, examine the substrate scope, and are directed toward functionalization of the allylation intermediate are described.
Woodward
Angela R
AR
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Burks
Heather E
HE
Chan
Louis M
LM
Morken
James P
JP
D000466:Alkadienes / Q000737:chemistry*; D000478:Alkylation; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D000466:Alkadienes; D001896:Boron Compounds; C025947:propadiene; D010165:Palladium