A reagent for hydroboration reduction and other applications.1,2 More stable than BH3THF but has an unpleasant odor. A borane source for oxazeborolidine catalyzed asymmetric reductions of ketones (Corey-Bakshi-Shibata Reduction).3 Used in the direct reduction of carboxylic acids to alcohols,4 in the study of the catalytic asymmetric borane reduction of both electron-deficient and electron-rich ketones with high enantioselectivity with a C3-symmetric chiral tris(β-hydroxy phosphoramide) ligand,5 hydroboration of ethoxy acetylene to generate tris(ethoxyvinyl) borane,6 conversion of various nucleophiles including alkylamines, arylamines, hydrazides, alcohols and phenols to the corresponding amides and esters in excellent yield,7 in the asymmetric reduction of indanones and tetralones,8 and CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols.9
References
1. J. Korean Chem. Soc. 2003, 47, 675.
2. Tetrahedron Asymmetry 2004, 15, 1495.
3. Org. Prep. Proced. Int. 1981, 13, 225.
4. J. Org. Chem. 1973, 38, 2786.
5. Org. Lett., 2006, 8, 1327.
6. Org. Lett., 2009, 11, 2117.
7. Synlett, 2007, 1026.
8. Tetrahedron Asymmetry 2006, 17, 2074.
9. Tetrahedron Asymmetry 2006, 17, 1824.