Literature DB >> 23436470

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

David Lebœuf1, Eric Theiste, Vincent Gandon, Stephanie L Daifuku, Michael L Neidig, Alison J Frontier.   

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.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID： 23436470      PMCID： PMC3887475          DOI： 10.1002/chem.201203396

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  27 in total

1.  Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Authors:  David Lebœuf; Jie Huang; Vincent Gandon; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-26       Impact factor: 15.336

2.  Tandem Nazarov cyclization-michael addition sequence catalyzed by an Ir(III) complex.

Authors:  Mesfin Janka; Wei He; Inga E Haedicke; Frank R Fronczek; Alison J Frontier; Richard Eisenberg
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

Review 3.  Advances in the Nazarov cyclization.

Authors:  Waka Nakanishi; Frederick G West
Journal:  Curr Opin Drug Discov Devel       Date:  2009-11

4.  Asymmetric Nazarov reaction catalyzed by chiral tris(oxazoline)/copper(II).

Authors:  Peng Cao; Chao Deng; You-Yun Zhou; Xiu-Li Sun; Jun-Cheng Zheng; Zuowei Xie; Yong Tang
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-14       Impact factor: 15.336

5.  Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate.

Authors:  Owen Scadeng; Michael J Ferguson; F G West
Journal:  Org Lett       Date:  2010-12-03       Impact factor: 6.005

6.  Substituent-controlled reactivity in the Nazarov cyclisation of allenyl vinyl ketones.

Authors:  Vanessa M Marx; Rhonda L Stoddard; Gavin S Heverly-Coulson; D Jean Burnell
Journal:  Chemistry       Date:  2011-06-07       Impact factor: 5.236

7.  Asymmetric Brønsted acid catalyzed carbonyl activation--organocatalytic domino electrocyclization-halogenation reaction.

Authors:  Magnus Rueping; Winai Ieawsuwan
Journal:  Chem Commun (Camb)       Date:  2011-09-05       Impact factor: 6.222

8.  Polarizing the Nazarov cyclization: the impact of dienone substitution pattern on reactivity and selectivity.

Authors:  Wei He; Ildiko R Herrick; Tulay A Atesin; Patrick A Caruana; Colleen A Kellenberger; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

9.  An expeditious Nazarov cyclization strategy toward the hydroazulene core of guanacastepene A.

Authors:  Pauline Chiu; Shuoliang Li
Journal:  Org Lett       Date:  2004-02-19       Impact factor: 6.005

10.  Predicting reactivity and stereoselectivity in the Nazarov reaction: a combined computational and experimental study.

Authors:  Andrea Cavalli; Alessandro Pacetti; Maurizio Recanatini; Cristina Prandi; Dina Scarpi; Ernesto G Occhiato
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
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