Palladium-catalyzed enantioselective diboration of prochiral allenes.
Pd-catalyzed diboration of prochiral allenes occurs exclusively at the internal position and is remarkably accelerated in the presence of Lewis basic ligand structures. On the basis of preliminary observations, a chiral ligand was employed, and the enantiomeric excess of a variety of diboration products was found to be in the range of 86-92% ee. The chiral diboron reaction products should be useful in organic synthesis, and preliminary experiments suggest that they may participate in allylation reactions with a high level of chirality transfer.
Pelz
Nicholas F
NF
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina, Chapel Hill, North Carolina 27599-3290, USA.
Woodward
Angela R
AR
Burks
Heather E
HE
Sieber
Joshua D
JD
Morken
James P
JP
D000466:Alkadienes / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D009943:Organophosphorus Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D001896:Boron Compounds; D009943:Organophosphorus Compounds; C434331:phosphoramidite; C025947:propadiene; D010165:Palladium