L-selectride

L-selectride

Chembox new
ImageFile = L-selectride.gif
ImageSize =
IUPACName = lithium tri-sec-butyl(hydrido)borate(1-)
OtherNames =
Section1 = Chembox Identifiers
CASNo = 38721-52-7
PubChem =
SMILES = [Li+] .CCC(C) [BH-] (C(C)CC)C(C)CC
Section2 = Chembox Properties
Formula = C12H28BLi
MolarMass = 190.10 g/mol
Appearance =
Density =
MeltingPt =
BoilingPt =
Solubility =
Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =

L-selectride, is an organic compound. 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. [cite journal | author = S. D. Knight, L. E. Overman and G. Pairaudeau | title = Synthesis applications of cationic aza-Cope rearrangements. 26. Enantioselective total synthesis of (-)-strychnine | year = 1993 | journal = J. Am. Chem. Soc. | volume = 115 | issue = 20 | pages = 9293–9294 | doi = 10.1021/ja00073a057]

L-selectride reduces enones by conjugate addition of hydride, since it is too bulky to attack directly at the carbonyl carbon. [cite book
last=Clayden
first=Jonathan
authorlink=:en:Jonathan Clayden
coauthors=Nick Greeves, Stuart Warren, Peter Wothers
title=Organic Chemistry
origyear=2001
edition=
publisher=Oxford University Press
isbn=0-19-850346-6
pages=p. 685
chapter=Alkylation of enolates]

N-selectride and K-selectride is the same compound but instead of lithium as cation they have sodium and potassium cations respectively.

References


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