Literature DB >> 19295905

Organocatalytic Highly Enantioselective Tandem Michael-Knoevenagel Reaction for the Synthesis of Substituted Thiochromanes.

Rajasekhar Dodda1, Tanmay Mandal, Cong-Gui Zhao.   

Abstract

Enantioenriched tetrasubstituted thiochromanes have been synthesized using a tandem Michael addition-Knoevenagel reaction between 2-mercaptobenzaldehydes and benzylidenemalonates with a 9-epi-aminoquinine thiourea derivative as the catalyst. Steric and electron effects were found to affect profoundly the enantioselectivity and diastereoselectivity of the reaction.

Entities:  

Year:  2008        PMID： 19295905      PMCID： PMC2350192          DOI： 10.1016/j.tetlet.2008.01.113

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  25 in total

1.  Organocatalytic asymmetric domino knoevenagel/diels-alder reactions: a bioorganic approach to the diastereospecific and enantioselective construction of highly substituted spiro[5,5]undecane-1,5,9-triones.

Authors:  D B Ramachary; Naidu S Chowdari; Carlos F Barbas
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-15       Impact factor: 15.336

2.  Cascade Michael--aldol reactions promoted by hydrogen bonding mediated catalysis.

Authors:  Liansuo Zu; Jian Wang; Hao Li; Hexin Xie; Wei Jiang; Wei Wang
Journal:  J Am Chem Soc       Date:  2007-02-07       Impact factor: 15.419

3.  Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.

Authors:  Brooks E Maki; Audrey Chan; Eric M Phillips; Karl A Scheidt
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

4.  Synthesis and pharmacological evaluation of thiopyran analogues of the dopamine D3 receptor-selective agonist (4aR,10bR)-(+)-trans-3,4,4a,10b-tetrahydro-4-n-propyl-2H,5H [1]b enzopyrano[4,3-b]-1,4-oxazin-9-ol (PD 128907).

Authors:  L A van Vliet; N Rodenhuis; D Dijkstra; H Wikström; T A Pugsley; K A Serpa; L T Meltzer; T G Heffner; L D Wise; M E Lajiness; R M Huff; K Svensson; S Sundell; M Lundmark
Journal:  J Med Chem       Date:  2000-07-27       Impact factor: 7.446

5.  Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions.

Authors:  Sven Brandau; Eddy Maerten; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

6.  Design, synthesis, and biological evaluation of conformationally restricted rivastigmine analogues.

Authors:  Maria Laura Bolognesi; Manuela Bartolini; Andrea Cavalli; Vincenza Andrisano; Michela Rosini; Anna Minarini; Carlo Melchiorre
Journal:  J Med Chem       Date:  2004-11-18       Impact factor: 7.446

7.  Asymmetric direct vinylogous Michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids.

Authors:  Dong Xue; Ying-Chun Chen; Qi-Wei Wang; Ling-Feng Cun; Jin Zhu; Jin-Gen Deng
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

8.  Heteroarotinoids. Synthesis, characterization, and biological activity in terms of an assessment of these systems to inhibit the induction of ornithine decarboxylase activity and to induce terminal differentiation of HL-60 cells.

Authors:  L W Spruce; S N Rajadhyaksha; K D Berlin; J B Gale; E T Miranda; W T Ford; E C Blossey; A K Verma; M B Hossain; D van der Helm
Journal:  J Med Chem       Date:  1987-08       Impact factor: 7.446

9.  Synthesis of Prolinal Dithioacetals as Catalysts for the Highly Stereoselective Michael Addition of Ketones and Aldehydes to beta-Nitrostyrenes.

Authors:  Tanmay Mandal; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2007       Impact factor: 2.415

10.  Inverse-electron-demand hetero-Diels-Alder reaction of beta,gamma-unsaturated alpha-ketophosphonates catalyzed by prolinal dithioacetals.

Authors:  Sampak Samanta; Jonathan Krause; Tanmay Mandal; Cong-Gui Zhao
Journal:  Org Lett       Date:  2007-06-09       Impact factor: 6.005
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  5 in total

1.  Enantioselective synthesis of bicylco[3.2.1]octan-8-ones using a tandem Michael-Henry reaction.

Authors:  Derong Ding; Cong-Gui Zhao; Qunsheng Guo; Hadi Arman
Journal:  Tetrahedron       Date:  2010-06-19       Impact factor: 2.457

2.  Developing novel organocatalyzed aldol reactions for the enantioselective synthesis of biologically active molecules.

Authors:  Mayur Bhanushali; Cong-Gui Zhao
Journal:  Synthesis (Stuttg)       Date:  2011-06       Impact factor: 3.157

3.  Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles.

Authors:  Sanjib Gogoi; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2009-05-13       Impact factor: 2.415

4.  Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines.

Authors:  Chittaranjan Bhanja; Satyaban Jena; Sabita Nayak; Seetaram Mohapatra
Journal:  Beilstein J Org Chem       Date:  2012-10-04       Impact factor: 2.883

Review 5.  (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers.

Authors:  Giorgos Koutoulogenis; Nikolaos Kaplaneris; Christoforos G Kokotos
Journal:  Beilstein J Org Chem       Date:  2016-03-10       Impact factor: 2.883
  5 in total

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