Literature DB >> 21155592

Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

William T Spencer1, Mark D Levin, Alison J Frontier.   

Abstract

A mild method for the diastereoselective formation of C(4), C(5)-disubstituted cyclopentenones has been developed, involving formation of a pentadienyl cation via diastereoselective oxidation of a vinyl alkoxyallene. Conrotatory electrocyclization provides the cyclopentenone product. The broad scope, mild conditions, and uncommon substitution pattern accessible through this transformation make it a useful addition to the existing repertoire of cyclopentenone synthetic methods.

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Year:  2010        PMID： 21155592      PMCID： PMC3032600          DOI： 10.1021/ol1027255

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

1.  An organocatalytic asymmetric Nazarov cyclization.

Authors:  Ashok K Basak; Naoyuki Shimada; William F Bow; David A Vicic; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

Review 2.  Advances in the Nazarov cyclization.

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

3.  A new approach to the nazarov reaction via sequential electrocyclic ring opening and ring closure.

Authors:  Tina N Grant; F G West
Journal:  J Am Chem Soc       Date:  2006-07-26       Impact factor: 15.419

4.  Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide.

Authors:  John A Malona; Kevin Cariou; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

5.  New synthetic approach to cyclopenta-fused heterocycles based upon a mild Nazarov reaction.

Authors:  Ernesto G Occhiato; Cristina Prandi; Alessandro Ferrali; Antonio Guarna; Paolo Venturello
Journal:  J Org Chem       Date:  2003-12-12       Impact factor: 4.354

6.  Spirodiepoxides: synthesis of epoxomicinoids.

Authors:  Yue Zhang; Joseph R Cusick; Partha Ghosh; Ning Shangguan; Sreenivas Katukojvala; Jennifer Inghrim; Thomas J Emge; Lawrence J Williams
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

7.  Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

Authors:  Gilles Lemière; Vincent Gandon; Kevin Cariou; Takahide Fukuyama; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  Org Lett       Date:  2007-04-25       Impact factor: 6.005

Review 8.  Enzymes in jasmonate biosynthesis - structure, function, regulation.

Authors:  Andreas Schaller; Annick Stintzi
Journal:  Phytochemistry       Date:  2009-08-22       Impact factor: 4.072

9.  Silver and Brønsted acid catalyzed nazarov-type cyclizations to generate benzofulvenes.

Authors:  Pierre Cordier; Corinne Aubert; Max Malacria; Emmanuel Lacôte; Vincent Gandon
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Silyl-substituted spirodiepoxides: stereoselective formation and regioselective opening.

Authors:  Partha Ghosh; Joseph R Cusick; Jennifer Inghrim; Lawrence J Williams
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005
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  9 in total

1.  Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors:  John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

2.  Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Authors:  David Lebœuf; Vincent Gandon; Jennifer Ciesielski; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2012-04-03       Impact factor: 15.419

3.  Biomimetic 2-Imino-Nazarov Cyclizations via Eneallene Aziridination.

Authors:  Joshua R Corbin; Devin R Ketelboeter; Israel Fernández; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2020-03-10       Impact factor: 15.419

4.  Diastereospecific nazarov cyclization of fully substituted dienones: generation of vicinal all-carbon-atom quaternary stereocenters.

Authors:  Anais Jolit; Saleta Vazquez-Rodriguez; Glenn P A Yap; Marcus A Tius
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-03       Impact factor: 15.336

5.  Cycloaromatization protocol for synthesis of polysubstituted phenol derivatives: method development and mechanistic studies.

Authors:  William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-08-14       Impact factor: 4.354

6.  Conjugate addition-initiated Nazarov cyclization.

Authors:  Joshua L Brooks; Patrick A Caruana; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

7.  α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors:  Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal:  Org Lett       Date:  2012-11-02       Impact factor: 6.005

8.  Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates.

Authors:  William T Spencer; Tulaza Vaidya; Alison J Frontier
Journal:  European J Org Chem       Date:  2013-06-01

9.  Advances in the chemistry of oxaziridines.

Authors:  Kevin S Williamson; David J Michaelis; Tehshik P Yoon
Journal:  Chem Rev       Date:  2014-04-22       Impact factor: 60.622
  9 in total

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