Literature DB >> 15844930

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

Michael Harmata1, Dong Reyoul Lee, Charles L Barnes.   

Abstract

[reaction: see text] Enol ethers are cleaved via a three-step sequence involving cycloaddition with dichloroketene, ring expansion with diazomethane, and a base-mediated retro-Nazarov reaction. The latter conrotatory process proceeds torquoselectively and stereospecifically in accord with theoretical predictions.

Entities:  

Year:  2005        PMID： 15844930     DOI： 10.1021/ol050657v

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


  5 in total

1.  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

2.  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

3.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

4.  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

5.  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
  5 in total

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