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Synlett 2009(12): 2037-2038  
DOI: 10.1055/s-0029-1217551
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Lithium tri-sec-Butylborohydride (l-Selectride): A Powerful and Highly Stereoselective Reducing Reagent

Hong-Juan Wang*
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, P. R. of China
e-Mail: wanghjchem@gmail.com;
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Publikationsdatum:
03. Juli 2009 (online)

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Introduction

Lithium tri-sec-butylborohydride (l-Selectride) is known to be an exceptionally powerful and highly stereoselective reducing agent. It has been used for the diastereoselective reduction of the ketones to give the alcohol, [¹-¹0] selective 1,4-reduction of the enones by conjugate addition of hydride to afford ketones [¹¹] [¹²] or alcohols, [¹³] conjugate reduction of exocyclic acrylonitrile derivatives, [¹4] reduction of the double bond [¹5] and iodide. [¹6] It was also found to be an efficient reagent for the desymmetrization of meso-­diesters, [¹7] dehalogenation of monohalopyridines, [¹8] rearrangement of 5-trimethylsilylthebaine, [¹9] reductive cleavage of exoxides, [²0] and deprotection of N-carbomethoxy-substituted opioids to N-noropioids. [²¹]

Lithium tri-sec-butylborohydride is commercially available, but can also 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. [²²]

Scheme 1