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ChemInform Abstract: X-Ray Crystal Structure, Conformation, and Preparation of anti-3,3,6,6-Tetramethylthiepane-4,5-diol: Stereochemistry of Reduction of a Heterocyclic α-Hydroxy Ketone.

✍ Scribed by N. FEEDER; M. J. GINNELLY; R. V. H. JONES; S. O'SULLIVAN; S. WARREN; P. WYATT

Book ID: 101863556
Publisher: John Wiley and Sons
Year: 2010
Weight: 37 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199813041

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✦ Synopsis

Stereochemistry of Reduction of a Heterocyclic α-Hydroxy Ketone.

-The stereoselectivity of the reduction of the hydroxyketone (I) using chelating and non-chelating reducing agents is studied. Whilst in most of the cases the syn-diol (II) is formed predominantly, the zinc-chelated DIBAL reduction proceeds with moderate anti-selectivity to afford substantial amounts of the anti-diol (III). Crossing from the syn-to the anti-series is achieved utilizing the Sharpless orthoester approach [→ (V)]. -(FEEDER, N.; GINNELLY, M.

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