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. 2011 Mar 18;76(6):1883-6.
doi: 10.1021/jo102294j. Epub 2011 Feb 4.

Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols

Kun Huang  1 , Haiyang Wang, Viatcheslav Stepanenko, Melvin De Jesús, Carilyn Torruellas, Wildeliz Correa, Margarita Ortiz-Marciales
Affiliations

Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols

Kun Huang et al. J Org Chem. .

Abstract

An enantioselective borane-mediated reduction of a variety of 2-haloketones with 10% spiroaminoborate ester 1 as catalyst is described. By a simple basic workup of 2-halohydrins, optically active epoxides are obtained in high yield and with excellent enantiopurity (up to 99% ee). Ring-opening of oxiranes with phenoxides or sodium azide is investigated under different reaction conditions affording nonracemic 1,2-hydroxy ethers and 1,2-azido alcohols with excellent enantioselectivity (99% ee) and in good to high chemical yield.

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Figures

FIGURE 1
FIGURE 1
Representative Aminoborate Complexes.
SCHEME 1
SCHEME 1
Ring-opening of Epoxides with NaN3 in Hot Water
See this image and copyright information in PMC

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