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. 2007 Nov 26;18(23):2738-2745.
doi: 10.1016/j.tetasy.2007.10.044.

Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols

Viatcheslav Stepanenko  1 , Melvin De Jesús, Wildeliz Correa, Irisbel Guzmán, Cindybeth Vázquez, Lymaris Ortiz, Margarita Ortiz-Marciales
Affiliations

Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols

Viatcheslav Stepanenko et al. Tetrahedron Asymmetry. .

Abstract

The effectiveness of several spiroborate ester catalysts was investigated in the asymmetric borane reduction of 2-, 3-, 4-acetylpyridines under different reaction conditions. Highly enantiomerically enriched 1-(2-, 3- and 4-pyridyl)ethanols and 1-(heterocyclic)ethanols were obtained using 1 to 10% catalytic loads of the spiroborate 5 derived from diphenylprolinol and ethylene glycol.

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Figures

Fig. 1
Fig. 1
Chiral spiroborates derived from non-racemic 1,2-aminoalcohols
Fig. 2
Fig. 2
Amount of catalyst 1 vs % ee of 1-(3-pyridyl)ethanol
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