8427. Selectride(R) (Aldrich)

Description and 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. Sch"onecker, J. Prakt. Chem. Chem.-Ztg. 338, 759-762 (1996).

Chemical structure

Derivative

L-Selectride.

Nomenclature

CAS number: 38721-52-7
Lithium (T-4)-hydrotris(1-methylpropyl)borate(1-); lithium tri-sec-butylborohydride.
C12H28BLi; mol wt 190.10.
C 75.82%, H 14.85%, B 5.69%, Li 3.65%.

Description and 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

K-Selectride.

Nomenclature

CAS number: 54575-49-4
Potassium (T-4)-hydrotris(1-methylpropyl)borate(1-); potassium tri-sec-butylborohydride.
C12H28BK; mol wt 222.26.
C 64.85%, H 12.70%, B 4.86%, K 17.59%.

Description and 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 α,β-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.