L-selectride

Structural formula
General
Surname	L-selectride
other names	Lithium tri- sec -butyl (hydrido) borate ( IUPAC ) Lithium tri- sec -butyl borohydride
Molecular formula	C 12 H 28 BLi
External identifiers / databases
CAS number 38721-52-7 EC number 254-101-1 ECHA InfoCard 100.049.166 PubChem 3611392 ChemSpider 2006 164 Wikidata Q116065
properties
Molar mass	190.10 g mol −1
safety instructions
GHS labeling of hazardous substances for the 1.0 M solution in THF danger H and P phrases H: 225-250-260-314-335 P: 210-222-223-231 + 232-370 + 378-422
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

L-selectride is a sterically hindered and therefore selective reducing agent for ketones and the brand name of the Sigma-Aldrich company for lithium tri- sec- butyl (hydrido) borate. It is available as a solution in THF . The brand name is much more common than the systematic name. It is used, for example, in permutation reactions . A comparison between the reactions carried out by L-selectride and MeTi (O ⁱ Pr) ₃ clarifies the background of a permutation reaction .

The reduction is usually carried out at low temperatures (−78 ° C). However, cases are known in which an increase in temperature leads to better stereoselectivity and even the reversal of selectivity.

Individual evidence

1. ↑ ^{a b} Data sheet L-Selectride ^® solution, 1.0 M in THF from Sigma-Aldrich , accessed on January 21, 2012 ( PDF ).
2. ↑ Parts of the labeling of hazardous substances relate to the hazards caused by the solvent.
3. ↑ Jerry March: Advanced Organic Chemistry , John Wiley & Sons, New York 1985, ISBN 0-471-88841-9 .
4. ^ Kai Oesterreich, Dietrich Spitzner, Tetrahedron , 2002 , 58 ; 4331-4334, doi: 10.1016 / S0040-4020 (02) 00336-8 .