Literature DB >> 32883082

Michael Addition with an Olefinic Pyridine: Organometallic Nucleophiles and Carbon Electrophiles.

Michael R Stentzel1, Douglas A Klumpp1.   

Abstract

The conjugate addition reactions of trans-1,2-di(2-pyridyl)ethylene have been studied. This substrate reacts with organolithium nucleophiles, and the resulting anionic intermediates may be trapped by proton or various carbonyl-based electrophiles. It is suggested that the dipyridyl structure stabilizes the intermediate carbanion, allowing the Michael adduct to be captured by an added electrophile.

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Year:  2020        PMID: 32883082      PMCID: PMC7781395          DOI: 10.1021/acs.joc.0c00823

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


  5 in total

1.  Bis annelations via 6-methyl-2-vinylpyridine. An efficient synthesis of dl-D-homoestrone.

Authors:  S Danishefsky; P Cain; A Nagel
Journal:  J Am Chem Soc       Date:  1975-01-22       Impact factor: 15.419

2.  Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles.

Authors:  Ke Zheng; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Rev       Date:  2018-07-26       Impact factor: 60.622

Review 3.  Conjugate addition-enantioselective protonation reactions.

Authors:  James P Phelan; Jonathan A Ellman
Journal:  Beilstein J Org Chem       Date:  2016-06-15       Impact factor: 2.883

4.  Highly enantioselective catalytic synthesis of chiral pyridines.

Authors:  Ravindra P Jumde; Francesco Lanza; Tilde Pellegrini; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2017-12-12       Impact factor: 14.919

Review 5.  Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes.

Authors:  Diego A Alonso; Alejandro Baeza; Rafael Chinchilla; Cecilia Gómez; Gabriela Guillena; Isidro M Pastor; Diego J Ramón
Journal:  Molecules       Date:  2017-05-29       Impact factor: 4.411

  5 in total

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