Reductive cyclodimerization of chalcones: exploring the "self-adaptability" of galvanostatic electrosynthesis

The "self-adaptability" of galvanostatic electrolysis was shown to assist a multistage unprecedented chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. The process, all involving the reductive events, delivered densely functionalized cyclopentanes feat...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-01, Vol.60 (4), p.404-407
Main Authors: Garbini, Mauro, Brunetti, Andrea, Pedrazzani, Riccardo, Monari, Magda, Marcaccio, Massimo, Bertuzzi, Giulio, Bandini, Marco
Format: Article
Language:English
Subjects:
Aldehydes
Electrolysis
Reaction mechanisms
Stereoselectivity
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Summary:The "self-adaptability" of galvanostatic electrolysis was shown to assist a multistage unprecedented chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. The process, all involving the reductive events, delivered densely functionalized cyclopentanes featuring five contiguous stereocenters (25 examples, yields of up to 95%, values up to >20 : 1). Dedicated and combined experimental as well as electrochemical investigation revealed the key role of a dynamic kinetic resolution of the aldol intermediate for the reaction mechanism.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc04920e