Literature DB >> 21780785

Conjugate addition-initiated Nazarov cyclization.

Joshua L Brooks1, Patrick A Caruana, Alison J Frontier.   

Abstract

A reaction sequence involving the 1,6-conjugate addition of a nucleophile to a dienyl diketone followed by Nazarov cyclization is described. Several nucleophiles are identified as competent initiators for the sequence. A different reaction outcome is observed when catalytic amounts of nucleophile are employed, involving elimination of the nucleophile after the electrocyclization.

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Year:  2011        PMID： 21780785      PMCID： PMC3178270          DOI： 10.1021/ja205440x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  18 in total

1.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
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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.  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

5.  Stereoselective synthesis of spirocyclic ketones by Nazarov reaction.

Authors:  Cristina Prandi; Annamaria Deagostino; Paolo Venturello; Ernesto G Occhiato
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

6.  Alpha-hydroxy cyclopentenones from alpha-diketones.

Authors:  William A Batson; Divakaramenon Sethumadhavan; Marcus A Tius
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

7.  Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

Authors:  William T Spencer; Mark D Levin; Alison J Frontier
Journal:  Org Lett       Date:  2010-12-14       Impact factor: 6.005

8.  Studies directed toward the synthesis of hamigeran B: a catalytic oxidative cyclization.

Authors:  Zhengxin Cai; Michael Harmata
Journal:  Org Lett       Date:  2010-11-16       Impact factor: 6.005

9.  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

10.  Nazarov cyclizations of an allenyl vinyl ketone with interception of the oxyallyl cation intermediate for the formation of carbon-carbon bonds.

Authors:  Vanessa M Marx; D Jean Burnell
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419
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  8 in total

1.  Neutral Nazarov-type cyclization catalyzed by palladium(0).

Authors:  Naoyuki Shimada; Craig Stewart; William F Bow; Anais Jolit; Kahoano Wong; Zhe Zhou; Marcus A Tius
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

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.  Enantioselective Nazarov Cyclization Catalyzed by a Cinchona Alkaloid Derivative.

Authors:  Yu-Wen Huang; Alison J Frontier
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Enyne diketones as substrate in asymmetric Nazarov cyclization for construction of chiral allene cyclopentenones.

Authors:  Shengbiao Tang; Peng Zhang; Ying Shao; Jiangtao Sun
Journal:  Nat Commun       Date:  2022-06-07       Impact factor: 17.694

5.  Cyclization cascades initiated by 1,6-conjugate addition.

Authors:  Joshua L Brooks; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2012-09-28       Impact factor: 15.419

6.  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

7.  No acid required: 4π and 6π electrocyclization reactions of dienyl diketones for the synthesis of cyclopentenones and 2H-Pyrans.

Authors:  Steven D Jacob; Joshua L Brooks; Alison J Frontier
Journal:  J Org Chem       Date:  2014-10-17       Impact factor: 4.354

8.  Ruthenium(ii)-catalyzed regioselective 1,6-conjugate addition of umpolung aldehydes as carbanion equivalents.

Authors:  Hyotaik Kang; Chao-Jun Li
Journal:  Chem Sci       Date:  2021-11-29       Impact factor: 9.825
  8 in total

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