Asymmetric Synthesis of Primary Amines via the Spiroborate-Catalyzed Borane Reduction of Oxime Ethers
- 31 March 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (9) , 1793-1795
- https://doi.org/10.1021/ol0704791
Abstract
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 °C resulting in complete conversion to the corresponding primary amine in up to 99% ee.Keywords
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