Literature DB >> 17081031

An N-heterocyclic carbene-catalyzed [8 + 3] annulation of tropone and enals via homoenolate.

Vijay Nair1, Manojkumar Poonoth, Sreekumar Vellalath, Eringathodi Suresh, Rajasekaran Thirumalai.   

Abstract

A novel protocol for the annulation of tropone to enals involving nucleophilic heterocyclic carbene (NHC) catalyzed homoenolate formation has been developed. Interestingly, the reaction led to bicyclic delta-lactones instead of the expected gamma-spirolactones, presumably by the uncommon [8 + 3] annulation pathway. The strategy works well with a variety of enals.

Entities:  

Year:  2006        PMID: 17081031     DOI: 10.1021/jo0615706

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


  11 in total

Review 1.  Carbene catalysts.

Authors:  Jennifer L Moore; Tomislav Rovis
Journal:  Top Curr Chem       Date:  2010

Review 2.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

3.  Synthesis of Naturally Occurring Tropones and Tropolones.

Authors:  Na Liu; Wangze Song; Casi M Schienebeck; Min Zhang; Weiping Tang
Journal:  Tetrahedron       Date:  2014-12-09       Impact factor: 2.457

4.  Protonation of Homoenolate Equivalents Generated by N-Heterocyclic Carbenes.

Authors:  Brooks E Maki; Audrey Chan; Karl A Scheidt
Journal:  Synthesis (Stuttg)       Date:  2008-04       Impact factor: 3.157

5.  The Jekyll-and-Hyde chemistry of Phaeobacter gallaeciensis.

Authors:  Mohammad R Seyedsayamdost; Rebecca J Case; Roberto Kolter; Jon Clardy
Journal:  Nat Chem       Date:  2011-02-27       Impact factor: 24.427

6.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

7.  Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams.

Authors:  Nicholas A White; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2013-05-28       Impact factor: 15.419

8.  Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropones.

Authors:  Pingfan Li; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

9.  Synthesis of Substituted Tropones by Sequential Rh-Catalyzed [5+2] Cycloaddition and Elimination.

Authors:  Wangze Song; Bao-Min Xi; Ka Yang; Weiping Tang
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

10.  Ni(NHC)]-catalyzed cycloaddition of diynes and tropone: apparent enone cycloaddition involving an 8π insertion.

Authors:  Puneet Kumar; Ashish Thakur; Xin Hong; K N Houk; Janis Louie
Journal:  J Am Chem Soc       Date:  2014-12-05       Impact factor: 15.419

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