Literature DB >> 19829750

Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction.

Rajasekhar Dodda1, Joshua J Goldman, Tanmay Mandal, Cong-Gui Zhao, Grant A Broker, Edward R T Tiekink.   

Abstract

Enantioenriched 2,3,4-trisubstituted thiochromanes have been synthesized by using a cupreine-catalyzed tandem Michael addition-Henry reaction between 2-mercaptobenzaldehydes and β-nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be further improved through a single recrystallization (up to 98% de and> 99% ee).

Entities:  

Year:  2008        PMID： 19829750      PMCID： PMC2760986          DOI： 10.1002/adsc.200700331

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  29 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

Review 2.  Catalytic asymmetric tandem transformations triggered by conjugate additions.

Authors:  Hong-Chao Guo; Jun-An Ma
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-09       Impact factor: 15.336

3.  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

4.  Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, tandem Michael/Henry reaction for the control of four stereocenters.

Authors:  Yujiro Hayashi; Tsubasa Okano; Seiji Aratake; Damien Hazelard
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  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

6.  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

7.  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

8.  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

9.  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

10.  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
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  7 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.  Mechanistic elucidation of the tandem Diels-Alder/(3 + 2) cycloadditions in the design and syntheses of heterosteroids.

Authors:  Benedicta Donkor; Abdul Rashid Umar; Ernest Opoku
Journal:  J Mol Model       Date:  2022-02-27       Impact factor: 1.810

4.  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

5.  Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael-Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis.

Authors:  Yan Zhang; Pornrapee Vongvilai; Morakot Sakulsombat; Andreas Fischer; Olof Ramström
Journal:  Adv Synth Catal       Date:  2014-03-03       Impact factor: 5.837

6.  Asymmetric domino synthesis of indanes bearing four contiguous stereocentres catalyzed by sub-mol% loadings of a squaramide in minutes.

Authors:  Charles C J Loh; Daniel Hack; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2013-11-11       Impact factor: 6.222

7.  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
  7 in total

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