Description
Lithium tri-sec-butylborohydride, commercially available as a one molar solution in tetrahydrofuran. It is widely used as a mild and strong reducing agent with high stereoselectivity in organic synthesis.
Features
Lithium tri-sec-butylborohydride is a new type of hydride reducing agent, which has the characteristics of strong reducing ability and high regio- and stereoselectivity.
Preparation
Lithium triisobutylhydroborate can be prepared by:In a 3000ml three-necked flask, add 1000ml of 1mol/L tri-sec-butylboron tetrahydrofuran solution, add 1000ml of 1mol/L triethylenediamine tetrahydrofuran solution simultaneously, introduce nitrogen to start stirring, put the mixture of the two in an ice-water bath After cooling to 0° C., 1000 ml of a 1 mol/L lithium aluminum hydride solution in tetrahydrofuran was slowly added dropwise to the above mixed solution with a constant pressure funnel for about 10 hours.
Physical properties
clear colourless solution
Uses
L-Selectride (Lithium triisobutylhydroborate) is used as a reducing agent. Reagent for: Enantioselective synthesis of a-amino acids via reduction of N-tert-butanesulfinyl ketimine esters. Diastereoselective reduction reactions. Hydride reduction of the Danishefsky pyranones. Asymmetric reductive aldol reaction of enones with a-alkoxy aldehydes. Synthesis of alkanols by carbonylation reactions.
Uses
L-Selectride Solution is a reducing agent which is used in the preparation of oxygen heterocycles. Used also as a reactant in the synthesis of novel bicicyclo[3.1.0]hexane analags which may prove useful in the treatment of depression.
Production Methods
L-Selectride can be readily prepared by addition of tri-sec-butylborane to a tetrahydrofuran solution of lithium aluminium hydride at room temperature. It is obtained as colorless solution in tetrahydrofuran
[1].
References
[1] H.J.-Wang. (2009). Lithium tri-sec-Butylborohydride (l-Selectride): A Powerful and Highly StereoselectiveReducing Reagent. Synlett, 34 1, 2037–2038.
https://doi.org/10.1055/S-0029-1217551
