L-selectride

L-selectride
IUPAC name

lithium tri-sec-butyl(hydrido)borate(1-)
Identifiers
CAS number 38721-52-7 Y
Jmol-3D images Image 1
Properties
Molecular formula C12H28BLi
Molar mass 190.10 g/mol
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

L-selectride is an organoborane. It is used in organic chemistry as a reducing agent, for example in the reduction of a ketone, as part of Overman's synthesis of strychnine.[1]

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.[2] L-Selectride can also stereoselectively reduce carbonyl groups in a 1,2-fashion, again due to the steric nature of the hydride reagent.[3]

N-selectride and K-selectride are related compounds, but instead of lithium as cation they have sodium and potassium cations respectively.

References

  1. ^ 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. 115 (20): 9293–9294. doi:10.1021/ja00073a057. 
  2. ^ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 685. ISBN 978-0-19-850346-0. 
  3. ^ Scott A. Miller and A. Richard Chamberlin (1989). "Highly selective formation of cis-substituted hydroxylactams via auxiliary-controlled reduction of imides". J. Org. Chem. 54 (11): 2502–2504. doi:10.1021/jo00272a004.