Title: Selectride® (Aldrich)
Literature References: Group of stereoselective trialkyl borohydride reducing agents. Reduction of cycloalkenones: J. M. Fortunato, B. Ganem, J. Org. Chem. 41, 2194 (1976). Review of synthetic applications: S. Wittmann, B. Schönecker, J. Prakt. Chem. Chem.-Ztg. 338, 759-762 (1996).
Derivative Type: L-Selectride
CAS Registry Number: 38721-52-7
CAS Name: Lithium (T-4)-hydrotris(1-methylpropyl)borate(1-)
Additional Names: lithium tri-sec-butylborohydride
Molecular Formula: C12H28BLi
Molecular Weight: 190.10
Percent Composition: C 75.82%, H 14.85%, B 5.69%, Li 3.65%
Literature References: Prepn and use in stereoselective reduction of cyclic ketones: H. C. Brown, S. Krishnamurthy, J. Am. Chem. Soc. 94, 7159 (1972). Synthetic use in reduction of cyclic anhydrides: M. A. Makhlouf, B. Rickborn, J. Org. Chem. 46, 4810 (1981); in cleavage of carbamates and O-demethylation of alkaloids: A. Coop et al., ibid. 63, 4392 (1998).
Derivative Type: K-Selectride
CAS Registry Number: 54575-49-4
CAS Name: Potassium (T-4)-hydrotris(1-methylpropyl)borate(1-)
Additional Names: potassium tri-sec-butylborohydride
Molecular Formula: C12H28BK
Molecular Weight: 222.26
Percent Composition: C 64.85%, H 12.70%, B 4.86%, K 17.59%
Literature References: Prepn: C. A. Brown, J. Am. Chem. Soc. 95, 4100 (1973); idem, Inorg. Synth. 17, 26 (1977). Synthetic use in conjugate reduction and reductive alkylation of a,b-unsaturated cyclohexenones: B. Ganem, J. Org. Chem. 40, 146 (1975); in reduction of diketo steroids: D. M. Tal et al., Tetrahedron 40, 851 (1984).
Properties: Prepd as a viscous, clear, water-white to yellow soln in THF. Reacts vigorously with water.
CAUTION: Solutions in THF may cause skin irritation and chemical burns (C. A. Brown, 1977).
Use: Mild reducing agents in organic synthesis. |