L-selectride

L-selectride
Names
	IUPAC name lithium tri-sec-butyl(hydrido)borate(1-)
Identifiers
CAS Number	38721-52-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	2006164 ;
ECHA InfoCard	100.049.166
EC Number	254-101-1;
PubChem CID	2723989;
UNII	J471N7T23N ;
CompTox Dashboard (EPA)	DTXSID70959536 ;
	InChI InChI=1S/C12H28B.Li/c1-7-10(4)13(11(5)8-2)12(6)9-3;/h10-13H,7-9H2,1-6H3;/q-1;+1 Key: ACJKNTZKEFMEAK-UHFFFAOYSA-N ; InChI=1/C12H28B.Li/c1-7-10(4)13(11(5)8-2)12(6)9-3;/h10-13H,7-9H2,1-6H3;/q-1;+1 Key: ACJKNTZKEFMEAK-UHFFFAOYAI;
	SMILES [Li+].CCC(C)[BH-](C(C)CC)C(C)CC;
Properties
Chemical formula	C12H28BLi
Molar mass	190.10 g/mol
Appearance	Colorless liquid
Density	0.870 g/ml
Solubility in water	Reacts violently with water
Hazards
Main hazards	Water reactive, flammable, burns skin and eyes
Flash point	-17 °F
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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. These reagents can sometimes be used as alternatives to, for instance, sodium amalgam reductions in inorganic chemistry.

Aprepitant is another synthesis example where L-selectride was used.

References

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.
Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 685. ISBN 978-0-19-850346-0.
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.

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[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.