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Asymmetric reduction of ketoxime ethers to optically active O-substituted hydroxylamines with reagents prepared from borane and chiral amino alcohols

✍ Scribed by John T. Dougherty; Joseph R. Flisak; Jerome Hayes; Ivan Lantos; Li Liu; Lynn Tucker

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 183 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00007-4

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✦ Synopsis

The asymmetric reduction of ketoxime ethers to yield enantiomerically enriched chiral hydroxylamines with reagents prepared from borane and norephedrine has been investigated. Very high enantioselectivity (ca. 99% ee) was obtained in the reduction of ketoxime O-(o-nitrobenzyl) ether to O-(o-nitrobenzyl) hydroxylamine.

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ChemInform Abstract: Asymmetric Reductio

ChemInform Abstract: Asymmetric Reduction of Ketoxime Ethers to Optically Active O- Substituted Hydroxylamines with Reagents Prepared from Borane and Chiral Amino Alcohols.

✍ J. T. DOUGHERTY; J. R. FLILSAK; J. HAYES; I. LANTOS; L. LIU; L. TUCKER 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

Asymmetric Reduction of Ketoxime Ethers to Optically Active O-Substituted Hydroxylamines with Reagents Prepared from Borane and Chiral Amino Alcohols. -The reduction in the presence of norephedrine is an efficient method to prepare chiral O-substituted hydroxylamines. However, O-Tbs and O-tBu subst