Literature DB >> 12868905

Formal intermolecular 4 + 4 approach to cyclooctanoids: 4 + 3 capture of the Nazarov oxyallyl intermediate with simple 1,3-dienes.

Yong Wang1, Brenden D Schill, Atta M Arif, F G West.   

Abstract

[reaction: see text] Simple 1,4-dien-3-ones and 1,3-dienes react in the presence of BF(3).OEt(2) via a domino Nazarov electrocyclization/intermolecular [4 + 3]-cycloaddition sequence to furnish keto-bridged cyclooctenes in good yield. Most cases showed high diastereofacial selectivity and/or endo/exo selectivity, and surprising levels of regioselectivity were observed when isoprene was used as the diene partner.

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Year:  2003        PMID： 12868905     DOI： 10.1021/ol034985b

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


  8 in total

1.  Intramolecular azide trapping of the Nazarov intermediate: formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation.

Authors:  Ali Rostami; Yong Wang; Atta M Arif; Robert McDonald; F G West
Journal:  Org Lett       Date:  2007-01-26       Impact factor: 6.005

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.  Oxyallyl exposed: an open-shell singlet with picosecond lifetimes in solution but persistent in crystals of a cyclobutanedione precursor.

Authors:  Gregory Kuzmanich; Fabian Spänig; Chao-Kuan Tsai; Joann M Um; Ryan M Hoekstra; K N Houk; Dirk M Guldi; Miguel A Garcia-Garibay
Journal:  J Am Chem Soc       Date:  2011-02-07       Impact factor: 15.419

4.  Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors:  Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal:  Org Lett       Date:  2012-03-13       Impact factor: 6.005

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.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

7.  Interrupting the Nazarov cyclization with indoles.

Authors:  Ashok K Basak; Marcus A Tius
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005

8.  Synthesis of Functionally Substituted Bicyclo[4.2.1]nona-2,4-dienes and Bicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-catalyzed [6π + 2π] Cycloaddition of 2-Tropylcyclohexanone.

Authors:  Gulnara N Kadikova; Lilya U Dzhemileva; Vladimir A D'yakonov; Usein M Dzhemilev
Journal:  ACS Omega       Date:  2020-11-24
  8 in total

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