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Asymmetric reduction of ketoxime derivatives and N-alkylketimines with borane–oxazaborolidine adducts

✍ Scribed by Marek P. Krzemiński; Marek Zaidlewicz

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
117 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

Oxime ethers of acetophenone, isopropyl methyl ketone, and tert-butyl methyl ketone were reduced to the corresponding hydroxylamine ethers of 45-94% ee with borane-oxazaborolidine 1 derived from (-)-norephedrine. A one-pot reduction of acetophenone oxime with 1 to 1-phenylethylhydroxylamine of 87% ee is described. The reduction of 6-methyl-2,3,4,5-tetrahydropyridine and N-methylimines of the above mentioned ketones with borane-B-methyloxazaborolidine adduct 2, derived from (-)-diphenylprolinol, gave the corresponding amines of 40-74% ee.

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