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Our knowledge of the biological relevance of regions of chemical space is shaped, in large part, by the synthetic accessibility of small molecules. Historically, however, chemists have explored chemical space in an exceptionally uneven and unsystematic way. We have previously demonstrated that metathesis cascade chemistry may be harnessed to yield small molecule collections with high scaffold diversity...
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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