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Asymmetric pinacol-type rearrangement of α-hydroxy methanesulfonates promoted by triethylaluminum — preparation of optically pure α-aryl and α-vinyl ketones —

✍ Scribed by Keisuke Suzuki; Eiji Katayama; Gen-ichi Tsuchihashi

Book ID: 104250284
Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 271 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)99831-4

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✦ Synopsis

Asymmetric (stereospecific) pinacol-type rearrangement of aryl or vinyl group in cl-hydroxy methanesulfonates is promoted by Et Al in CH2C12 at -78°C to afford optically pure a-aryl or a-vinyl keto ;T es.

Pinacol rearrangement is a fundamental process in organic chemistry and one of the powerful methods for the synthesis of ketones. 1) However, the scope

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Asymmetric synthesis of optically pure α-methyl-β,γ-unsaturated ketones via triethylaluminum-mediated stereospecific pinacol rearrangement of alkenyl groups

✍ Keisuke Suzuki; Eiji Katayama; Gen-ichi Tsuchihashi 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 255 KB

OpticalZy pure a-methyZ-@,y-unsaturated ketones are synthesized by the Et3Al-mediated pinacoZ-type rearrangement where alkenyl groups migrate stereospecificaZ2y with complete retention of the oZefin-geometry.