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Reductive pinacol-type rearrangement of chiral α-mesyloxy ketones promoted by organoaluminum compounds

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

Book ID
107858369
Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
268 KB
Volume
25
Category
Article
ISSN
0040-4039

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Asymmetric synthesis of chiral synthons
Asymmetric synthesis of chiral synthons bearing alkynyl group via organoaluminum-promoted pinacol-type rearrangement
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A method is described for the synthesis of chiral alkynyl ketones and alkynols via trimethylaluminum-promoted pinacol-type rearrangement where alkynyl groups behave as "the staying group", followed by stereoselective reduction leading to the latter.

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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 me