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. 2007 Apr 26;9(9):1793-5.
doi: 10.1021/ol0704791. Epub 2007 Mar 31.

Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers

Xiaogen Huang  1 , Margarita Ortiz-Marciales, Kun Huang, Viatcheslav Stepanenko, Francisco G Merced, Angel M Ayala, Wildeliz Correa, Melvin De Jesús
Affiliations

Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers

Xiaogen Huang et al. Org Lett. .

Abstract

[reaction: see text] The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 5-10 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% of catalyst 5 derived from diphenylvalinol in dioxane at 0 degrees C resulting in complete conversion to the corresponding primary amine in up to 99% ee.

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Figures

Figure 1
Figure 1
Spiroborate esters derived from non-racemic 1,2-amino alcohols
Scheme 1
Scheme 1
See this image and copyright information in PMC

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