Literature DB >> 20730196

Organocatalytic synthesis of spiro compounds via a cascade Michael-Michael-aldol reaction.

Xavier Companyó1, Alex Zea, Andrea-Nekane R Alba, Andrea Mazzanti, Albert Moyano, Ramon Rios.   

Abstract

The synthesis of spiro compounds via a Michael-Michael-aldol reaction is reported. The reaction affords spirooxindole derivatives in good yields and in almost diastereo- and enantiopure form. Moreover, the reaction works with several heterocycles such as oxindoles, benzofuranones, pyrazolones or azlactones rendering the final spiro compounds in good yields and excellent stereoselectivities.

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Year:  2010        PMID: 20730196     DOI: 10.1039/c0cc01522a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  12 in total

1.  A general organocatalyzed Michael-Michael cascade reaction generates functionalized cyclohexenes.

Authors:  Patrick G McGarraugh; Joshua H Jones; Stacey E Brenner-Moyer
Journal:  J Org Chem       Date:  2011-07-08       Impact factor: 4.354

2.  Enantioselective Synthesis of Spiro[cyclohexane-1,3'-indolin]-2'-ones Containing Multiple Stereocenters via Organocatalytic Michael/Aldol Cascade Reactions.

Authors:  Arun K Ghosh; Bing Zhou
Journal:  Tetrahedron Lett       Date:  2013-05-08       Impact factor: 2.415

3.  Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans.

Authors:  Jingqi Wang; Erika A Crane; Karl A Scheidt
Journal:  Org Lett       Date:  2011-05-18       Impact factor: 6.005

Review 4.  Molecular diversity of spirooxindoles. Synthesis and biological activity.

Authors:  Tetyana L Pavlovska; Ruslan Gr Redkin; Victoria V Lipson; Dmytro V Atamanuk
Journal:  Mol Divers       Date:  2015-09-29       Impact factor: 2.943

Review 5.  Recent advances in the development of polycyclic skeletons via Ugi reaction cascades.

Authors:  Jie Lei; Jiang-Ping Meng; Dian-Yong Tang; Brendan Frett; Zhong-Zhu Chen; Zhi-Gang Xu
Journal:  Mol Divers       Date:  2018-01-16       Impact factor: 2.943

6.  Streocontrolled construction of six vicinal stereogenic centers on spiropyrazolones via organocascade Michael/Michael/1,2-addition reactions.

Authors:  Pankaj Chauhan; Suruchi Mahajan; Charles C J Loh; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-05-19       Impact factor: 6.005

7.  Synergistic catalysis: cis-cyclopropanation of benzoxazoles.

Authors:  Marta Meazza; Mark E Light; Andrea Mazzanti; Ramon Rios
Journal:  Chem Sci       Date:  2015-10-30       Impact factor: 9.825

8.  Enantioselective Michael addition of 3-aryl-substituted oxindoles to methyl vinyl ketone catalyzed by a binaphthyl-modified bifunctional organocatalyst.

Authors:  Hyun Joo Lee; Saet Byeol Woo; Dae Young Kim
Journal:  Molecules       Date:  2012-06-18       Impact factor: 4.411

9.  Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis.

Authors:  Daniel Hack; Alexander B Dürr; Kristina Deckers; Pankaj Chauhan; Nico Seling; Lukas Rübenach; Lucas Mertens; Gerhard Raabe; Franziska Schoenebeck; Dieter Enders
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-16       Impact factor: 15.336

10.  Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones.

Authors:  Guo-Peng Wang; Yao-Liang Sun; Shou-Fei Zhu; Yin Wei; Qi-Lin Zhou; Min Shi
Journal:  Chem Sci       Date:  2015-09-15       Impact factor: 9.825

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