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Optically Active Epoxy Diols by Titanium-Catalyzed Oxidation of Enantiomerically Enriched Hydroperoxy and Hydroxy Homoallylic Alcohols

✍ Scribed by Waldemar Adam; Marion N. Korb; Chantu R. Saha-Möller

Book ID: 102657849
Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 507 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199805)1998:5<907::aid-ejoc907>3.0.co;2-f

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✦ Synopsis

The Ti-catalyzed epoxidation of optically active (S,S)-hydroperoxy homoallylic alcohols 2 affords the epoxy diol (S,R,S)-4 in high diastereoselectivity (d.r. up to 95:5), while the optically active hydroxy homoallylic alcohols (R,R)-3 are epoxidized by the β-hydroperoxy alcohol 5 under titanium catalysis to the corresponding epoxy (R,S,R)-diol 4 in a diastereomeric

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