Literature DB >> 18808186

Traceless chiral auxiliaries for the allene ether Nazarov cyclization.

April R Banaag1, Marcus A Tius.   

Abstract

The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.

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Year:  2008        PMID： 18808186      PMCID： PMC2674073          DOI： 10.1021/jo801503c

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  29 in total

1.  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

2.  Stereoselective Nazarov cyclizations of bridged bicyclic dienones.

Authors:  Robert D Mazzola; Timothy D White; Heidi R Vollmer-Snarr; F G West
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

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.  A convenient two step protocol for the synthesis of cyclopentenones and indanones, including an asymmetric variant.

Authors:  Daniel J Kerr; Christiane Metje; Bernard L Flynn
Journal:  Chem Commun (Camb)       Date:  2003-06-21       Impact factor: 6.222

5.  Construction of aryl-substituted triquinanes through the interrupted Nazarov reaction.

Authors:  Curtis J Rieder; Ryan J Fradette; F G West
Journal:  Chem Commun (Camb)       Date:  2008-02-25       Impact factor: 6.222

6.  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

7.  Cationic cyclopentannelation of allene ethers.

Authors:  Marcus A Tius
Journal:  Acc Chem Res       Date:  2003-04       Impact factor: 22.384

8.  Stereoselective C-glycosylation reactions of pyranoses: the conformational preference and reactions of the mannosyl cation.

Authors:  Claudia G Lucero; K A Woerpel
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

9.  Asymmetric cyclopentannelation: camphor-derived auxiliary.

Authors:  Paul E Harrington; Tsuyoshi Murai; Chester Chu; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2002-08-28       Impact factor: 15.419

10.  Total synthesis of (+/-)-terpestacin and (+/-)-11-epi-terpestacin.

Authors:  Gideon O Berger; Marcus A Tius
Journal:  J Org Chem       Date:  2007-07-14       Impact factor: 4.354
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  8 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.  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.  Asymmetric Nazarov Cyclizations.

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

5.  Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors:  Jie Huang; David Lebœuf; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-04-05       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.  Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

Authors:  William F Bow; Ashok K Basak; Anais Jolit; David A Vicic; Marcus A Tius
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

8.  Mixed aggregates of 1-methoxyallenyllithium with lithium chloride.

Authors:  Lawrence M Pratt; Darryl D Dixon; Marcus A Tius
Journal:  ChemistryOpen       Date:  2014-11-19       Impact factor: 2.911
  8 in total

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