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Efficient Nazarov cyclization/Wagner-Meerwein rearrangement terminated by a Cu(II)-promoted oxidation: synthesis of 4-alkylidene cyclopentenones.

ABSTRACT: The discovery and elucidation of a new Nazarov cyclization/Wagner-Meerwein rearrangement/oxidation sequence is described that constitutes an efficient strategy for the synthesis of 4-alkylidene cyclopentenones. DFT computations and EPR experiments were conducted to gain further mechanistic insight into the reaction pathways.

SUBMITTER: Lebœuf D

PROVIDER: S-EPMC3887475 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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Efficient Nazarov cyclization/Wagner-Meerwein rearrangement terminated by a Cu(II)-promoted oxidation: synthesis of 4-alkylidene cyclopentenones.

Lebœuf David D Theiste Eric E Gandon Vincent V Daifuku Stephanie L SL Neidig Michael L ML Frontier Alison J AJ

Chemistry (Weinheim an der Bergstrasse, Germany) 20130221 15

The discovery and elucidation of a new Nazarov cyclization/Wagner-Meerwein rearrangement/oxidation sequence is described that constitutes an efficient strategy for the synthesis of 4-alkylidene cyclopentenones. DFT computations and EPR experiments were conducted to gain further mechanistic insight into the reaction pathways. ...[more]

PMID: 23436470

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