Literature DB >> 21739949

Highly regioselective intermolecular hydroacylations of enamides with salicylaldehydes.

Hui-Jun Zhang1, Carsten Bolm.   

Abstract

Highly regioselective intermolecular hydroacylations of enamides under rhodium catalysis with monodentate phosphane ligands are reported for the first time. The presence of MeCN facilitates this novel C-C bond formation, and the electron-deficient phosphine P(p-F-Ph)(3) has proven most effective for the direct hydroacylation of 1-vinyl-2-pyrrolidinone. Accordingly, an atom-economic synthetic route to α-amido ketones from readily available substrates has been developed.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID： 21739949     DOI： 10.1021/ol201431c

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


  9 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.

Authors:  Xiang-Wei Du; Levi M Stanley
Journal:  Org Lett       Date:  2015-06-22       Impact factor: 6.005

3.  Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes.

Authors:  Kevin G M Kou; Lauren E Longobardi; Vy M Dong
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

4.  Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354

5.  Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

Authors:  Manjeet K Majhail; Paul M Ylioja; Michael C Willis
Journal:  Chemistry       Date:  2016-04-23       Impact factor: 5.236

6.  Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis.

Authors:  Robert N Straker; Manjeet K Majhail; Michael C Willis
Journal:  Chem Sci       Date:  2017-10-05       Impact factor: 9.825

7.  Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes.

Authors:  Sangwon Seo; Ming Gao; Eva Paffenholz; Michael C Willis
Journal:  ACS Catal       Date:  2021-05-05       Impact factor: 13.084

8.  2-Aminobenzaldehydes as versatile substrates for rhodium-catalyzed alkyne hydroacylation: application to dihydroquinolone synthesis.

Authors:  Matthias Castaing; Sacha L Wason; Beatriz Estepa; Joel F Hooper; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

9.  Traceless Rhodium-Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of β-Aryl Ketones.

Authors:  Anaïs Bouisseau; Ming Gao; Michael C Willis
Journal:  Chemistry       Date:  2016-09-26       Impact factor: 5.236
  9 in total

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