Literature DB >> 24002922

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

Anais Jolit1, Saleta Vazquez-Rodriguez, Glenn P A Yap, Marcus A Tius.   

Abstract

No vacancy: Fully substituted dienones that are highly polarized by a vinylogous carbonate group were found to undergo a remarkably rapid and diastereospecific Nazarov cyclization that led to cyclopentenones with vicinal all-carbon-atom quaternary centers (see example; SEM=2-(trimethylsilyl)ethoxymethyl, Tf=trifluoromethanesulfonyl).
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Nazarov cyclization; diastereoselectivity; quaternary stereocenters; rearrangement; synthetic methods

Mesh：

Substances：

Year:  2013        PMID： 24002922      PMCID： PMC3872134          DOI： 10.1002/anie.201305218

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  16 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

Review 2.  Advances in the Nazarov cyclization.

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

3.  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

4.  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

5.  Asymmetric Nazarov Cyclizations.

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

6.  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

7.  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

8.  Total synthesis of (+/-)-perophoramidine.

Authors:  James R Fuchs; Raymond L Funk
Journal:  J Am Chem Soc       Date:  2004-04-28       Impact factor: 15.419

9.  Stereoselective synthesis of acetoacetate-derived enol triflates.

Authors:  David Babinski; Omid Soltani; Doug E Frantz
Journal:  Org Lett       Date:  2008-06-10       Impact factor: 6.005

10.  Construction of α-amido-indanones via formal allenamide hydroacylation-Nazarov cyclization.

Authors:  Yen-Ku Wu; Tianmin Niu; F G West
Journal:  Chem Commun (Camb)       Date:  2012-08-06       Impact factor: 6.222
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  2 in total

1.  Retracted Article: An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions.

Authors:  Hongshe Wang; Weixing Zhao; Juan Du; Fenyan Wei; Qi Chen; Xiaomei Wang
Journal:  RSC Adv       Date:  2019-02-12       Impact factor: 3.361

2.  An efficient approach to angular tricyclic molecular architecture via Nazarov-like cyclization and double ring-expansion cascade.

Authors:  Yun-Peng Wang; Kun Fang; Yong-Qiang Tu; Jun-Jie Yin; Qi Zhao; Tian Ke
Journal:  Nat Commun       Date:  2022-04-28       Impact factor: 17.694
  2 in total

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