Literature DB >> 19459619

Nucleophilic heterocyclic carbene catalyzed annulation of enals to chalcones in methanol: a stereoselective synthesis of highly functionalized cyclopentanes.

Vijay Nair1, Beneesh P Babu, Sreekumar Vellalath, Vimal Varghese, Anabha E Raveendran, Eringathodi Suresh.   

Abstract

Homoenolates generated from enals by nucleophilic heterocyclic carbene (NHC) catalysis undergo annulation with chalcones in methanol to afford methyl beta-hydroxycyclopentanecarboxylates, stereoselectively. Construction of four contiguous stereocenters in a stereoselective manner is noteworthy.

Entities:  

Year:  2009        PMID： 19459619     DOI： 10.1021/ol900571x

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


  13 in total

1.  NHC-catalyzed/titanium(IV)-mediated highly diastereo- and enantioselective dimerization of enals.

Authors:  Daniel T Cohen; Benoit Cardinal-David; John M Roberts; Amy A Sarjeant; Karl A Scheidt
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

2.  Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators.

Authors:  Henrik Sundén; Linda Ta; Anton Axelsson
Journal:  J Vis Exp       Date:  2015-11-27       Impact factor: 1.355

3.  Cooperative N-heterocyclic carbene/Lewis acid catalysis for highly stereoselective annulation reactions with homoenolates.

Authors:  Benoit Cardinal-David; Dustin E A Raup; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

Review 4.  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

Review 5.  Chalcone: A Privileged Structure in Medicinal Chemistry.

Authors:  Chunlin Zhuang; Wen Zhang; Chunquan Sheng; Wannian Zhang; Chengguo Xing; Zhenyuan Miao
Journal:  Chem Rev       Date:  2017-05-10       Impact factor: 60.622

6.  An N-heterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirooxindole lactones.

Authors:  Julien Dugal-Tessier; Elizabeth A O'Bryan; Thomas B H Schroeder; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

7.  N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.

Authors:  Xiaodan Zhao; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

8.  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

9.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

10.  Cooperative Lewis acid/N-heterocyclic carbene catalysis.

Authors:  Daniel T Cohen; Karl A Scheidt
Journal:  Chem Sci       Date:  2012-01-01       Impact factor: 9.825
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