Journal
ORGANIC LETTERS
Volume 9, Issue 9, Pages 1793-1795Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0704791
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Funding
- NCRR NIH HHS [P20 RR016470-07, P20 RR016470-06] Funding Source: Medline
- NIGMS NIH HHS [GM-08216, S06 GM008216-250004, S06 GM008216] Funding Source: Medline
- OCPHP CDC HHS [P20 PR-016470] Funding Source: Medline
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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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