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ChemInform Abstract: High 1,6-Diastereoselectivity in the Hydride Reduction of an Acyclic Ketone Substrate via Bicyclic Chelation Control.

✍ Scribed by H.-C. ZHANG; B. D. HARRIS; C. A. MARYANOFF; B. E. MARYANOFF

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199706058

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✦ Synopsis

High 1,6-Diastereoselectivity in the Hydride Reduction of an Acyclic Ketone Substrate via Bicyclic Chelation Control.

-Reduction of the .epsilon.-hydroxyketone (I) with (R)-Alpine hydride provides the corresponding diol (II) with strong preponderance of the anti-diastereomer. The high degree of stereoselectivity is attributed to bicyclic chelation control of hydride addition. The degree of stereoselectivity depends on the distance between the hydroxyl and amine groups (cf. (I)/(III)) and decreases by methylation of the free hydroxy group in (I) (cf. (IV)). -(

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