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Palladium-catalyzed selective activation of allyl alcohols as allyl cations, allyl anions, and zwitterionic trimethylenemethanes


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Title: Palladium-catalyzed selective activation of allyl alcohols as allyl cations, allyl anions, and zwitterionic trimethylenemethanes
Authors: Kimura, Masanari / Tamaru, Yoshinao
Issue Date: May-2008
Publisher: International Union of Pure and Applied Chemistry
Citation: Pure and Applied Chemistry, 80(5), pp.979–991; 2008
Abstract: Pd-Et3B catalytic system promotes the generation of allyl cations, allyl anions, and zwitterionic trimethylenemethane species from the corresponding allylic alcohols. Allyl cations react with a wide variety of nucleophiles, e.g., amines, active methylene compounds, 1,3,5-trihydroxybenzene, indoles, aldehydes (at the alpha;-position). The reaction is extended to dehydrative Grob fragmentation of 1,3-diols. Allyl anions react with aldimines to give homoallyl amines. Zwitterionic trimethylenemethane, generated from 2-mefhylene-1,3-propanediol, reacts with aldehydes and aldimines to provide 3-methylenecyclopentanols and 3-methylenepyrrolidines, respectively. Vinyl epoxide can be utilized as a synthetic equivalent of 3-butenyl 2-anion-1-cation.
Keywords: allyl alcohols / allyl cations / catalysis / palladium / triethylborane / trimethylenemethane / umpolung / allyl anions
URI: http://hdl.handle.net/10069/18700
ISSN: 00334545
DOI: 10.1351/pac200880050979
Rights: © 2008 IUPAC
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/18700

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