Boron Lewis acids in organic synthesis

AEI 84

George W. Kabalka, kabalka@utk.edu1, Min-Liang Yao, yao@ion.chem.utk.edu2, and Scott Borella, borella@ion.chem.utk.edu2. (1) Departments of Chemistry and Radiology, The University of Tennessee, Buehler Hall, Knoxville, TN 37996-1600, (2) Departments of Chemistry and Radiology, University of Tennessee, Buehler Hall, Knoxville, TN 37996
The application of boron Lewis acids to carbon-carbon bond forming reactions continues to be an active research area due to their relatively low cost as well as the high selectivity and atom economy of the coupling reactions. Research in our laboratory has demonstrated that readily available aliphatic alcohols can be used as precursors in carbon-carbon bond forming reactions with both alkenylboron dihalides and alkynylboron dihalides. The direct substitution of aliphatic alcohols with allyl moieties also has been reported. It is believed that these Lewis acid induced reactions proceed through a cationic intermediate derived from boron mediated, carbon-oxygen bond cleavage. In addition, the reaction of alkenylboron dihalides or dialkenylboron halides with aldehydes produce stereodefined 1,5-dihalo-1,4-dienes in excellent yields with high Z,Z and Z,E stereoselectivity. The effects of the sequence of reagent addition and reaction temperature on the resultant stereochemistry will also be discussed.