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L-selectride

L-selectride is a organoboron compound with the chemical formula . A colorless salt, it is usually dispensed as a solution in THF. As a particularly basic and bulky borohydride, it is used for stereoselective reduction of ketones to alcohols.

Use in synthesis

Like other borohydrides, reductions are effected in two steps: delivery of the hydride equivalent to give the lithium alkoxide followed by hydrolytic workup: : :

The selectivity of this reagent is illustrated by its reduction of all three methylcyclohexanones to the less stable methylcyclohexanols in 98% yield.

Under certain conditions, L-selectride can selectively reduce enones by conjugate addition of hydride, owing to the greater steric hindrance the bulky hydride reagent experiences at the carbonyl carbon relative to the (also-electrophilic) β-position. L-Selectride can also stereoselectively reduce carbonyl groups in a 1,2-fashion, again due to the steric nature of the hydride reagent.

References

References

  1. (2012). "Encyclopedia of Reagents for Organic Synthesis".
  2. S. D. Knight, L. E. Overman and G. Pairaudeau. (1993). "Synthesis applications of cationic aza-Cope rearrangements. 26. Enantioselective total synthesis of (−)-strychnine". [[J. Am. Chem. Soc.]].
  3. {{Clayden
  4. Scott A. Miller and A. Richard Chamberlin. (1989). "Highly selective formation of cis-substituted hydroxylactams via auxiliary-controlled reduction of imides". [[J. Org. Chem.]].
  5. (1979). "Synthesis of metal carbonyl monoanions by trialkylborohydride cleavage of metal carbonyl dimers: A convenient one-flask preparation of metal alkyls, metal acyls, and mixed-metal compounds". Inorganic Chemistry.
  6. (2001). "Encyclopedia of Reagents for Organic Synthesis (EROS)".
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borohydrides organolithium-compounds reducing-agents sec-butyl-compounds
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