Literature DB >> 20030316

Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

William F Bow1, Ashok K Basak, Anais Jolit, David A Vicic, Marcus A Tius.   

Abstract

The mono-triflate salts of some chiral nonracemic 1,2-diamines react with alpha-ketoenones in a stoichiometric reaction to form products of the Nazarov cyclization in high enantiomeric ratios. The mechanism appears to involve rearrangement of an enamine-iminium ion.

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Year:  2010        PMID： 20030316      PMCID： PMC2854558          DOI： 10.1021/ol9025765

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


  28 in total

1.  Ni(II)-catalyzed enantioselective Nazarov cyclizations.

Authors:  Irene Walz; Antonio Togni
Journal:  Chem Commun (Camb)       Date:  2008-07-17       Impact factor: 6.222

2.  Stereospecific synthesis of dienones via a torquoselective retro-Nazarov reaction.

Authors:  Michael Harmata; Dong Reyoul Lee; Charles L Barnes
Journal:  Org Lett       Date:  2005-04-28       Impact factor: 6.005

3.  Catalytic asymmetric Nazarov reactions promoted by chiral Lewis acid complexes.

Authors:  Varinder K Aggarwal; Andrew J Belfield
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

4.  Efficient Nazarov cyclizations of 2-alkoxy-1,4-pentadien-3-ones.

Authors:  Guangxin Liang; Stefan N Gradl; Dirk Trauner
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

5.  Domino electrocyclization/azide-capture/schmidt rearrangement of dienones: one-step synthesis of dihydropyridones from simple building blocks.

Authors:  Dong Song; Ali Rostami; F G West
Journal:  J Am Chem Soc       Date:  2007-09-08       Impact factor: 15.419

6.  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

7.  Intermolecular reaction of internal alkynes and imines: propargyl tosylates as key partners in a gold-catalyzed [4 + 1] unusual cyclization leading to cyclopent-2-enimines.

Authors:  Samuel Suárez-Pantiga; Eduardo Rubio; Carmen Alvarez-Rúa; José M González
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

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.  Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

Authors:  Christopher Uyeda; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

10.  Asymmetric direct aldol reactions of pyruvic derivatives.

Authors:  Sanzhong Luo; Hui Xu; Liujuan Chen; Jin-Pei Cheng
Journal:  Org Lett       Date:  2008-04-08       Impact factor: 6.005
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  18 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.  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

3.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

4.  Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles.

Authors:  Mirza A Saputra; Binod Nepal; Nitin S Dange; Pu Du; Frank R Fronczek; Revati Kumar; Rendy Kartika
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-23       Impact factor: 15.336

5.  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

6.  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

7.  (2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus.

Authors:  Yunfan Zou; Jocelyn G Millar; J Scott Blackwood; Ryan Van Duzor; Lawrence M Hanks; Judith A Mongold-Diers; Joseph C H Wong; Ann M Ray
Journal:  J Chem Ecol       Date:  2015-07-07       Impact factor: 2.626

8.  Asymmetric Nazarov Cyclizations.

Authors:  Naoyuki Shimada; Craig Stewart; Marcus A Tius
Journal:  Tetrahedron       Date:  2011-08-19       Impact factor: 2.457

9.  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

10.  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
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