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ChemInform Abstract: Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation.

✍ Scribed by A. R. KATRITZKY; D. CHENG; S. A. HENDERSON; J. LI

Publisher: John Wiley and Sons
Year: 2010
Weight: 39 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199909071

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✦ Synopsis

Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation.

-A convenient and stereocontrolled olefination of aldehydes and ketones is developed by reacting the carbonyl compounds with lithiated benzotriazole derivatives followed by low-valent titanium (LVT) mediated dehydroxybenzotriazolylation. This method offers good stereoselectivity without any need to isolate diastereomeric intermediates and complements the Wittig, Peterson and Julia reactions. A variety of methods for the generation of the LVT reagent is also investigated, starting either from TiCl 3 or from TiCl 4 , which is more readily available from commercial sources.

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