Literature DB >> 22359347

Regioselective cycloaddition of 3-azetidinones and 3-oxetanones with alkynes through nickel-catalysed carbon-carbon bond activation.

Kelvin Y T Ho1, Christophe Aïssa.   

Abstract

Get in the ring! The first examples of transition-metal-catalysed C-C bond activation of 3-azetidinones and 3-oxetanones are reported. In the presence of a nickel catalyst and alkynes, a regioselective and high-yielding [4+2] cycloaddition occurs, leading to the formation of pyridinones, pyranones and eventually 4,5-disubstituted 3-hydroxypyridines (see scheme).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22359347     DOI: 10.1002/chem.201200167

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  11 in total

1.  An expeditious route to eight-membered heterocycles by nickel-catalyzed cycloaddition: low-temperature C(sp)2-C(sp)3 bond cleavage.

Authors:  Puneet Kumar; Kainan Zhang; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-17       Impact factor: 15.336

2.  Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides.

Authors:  Matthias Bender; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  Science       Date:  2017-08-25       Impact factor: 47.728

3.  A single step approach to piperidines via Ni-catalyzed β-carbon elimination.

Authors:  Puneet Kumar; Janis Louie
Journal:  Org Lett       Date:  2012-04-02       Impact factor: 6.005

4.  Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

Authors:  Ashish Thakur; Megan E Facer; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

5.  The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides.

Authors:  Timothy K Lane; Minh H Nguyen; Brendan R D'Souza; Nathan A Spahn; Janis Louie
Journal:  Chem Commun (Camb)       Date:  2013-09-11       Impact factor: 6.222

6.  A catalytic asymmetric synthesis of polysubstituted piperidines using a rhodium(I)-catalyzed [2+2+2] cycloaddition employing a cleavable tether.

Authors:  Timothy J Martin; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-19       Impact factor: 15.336

Review 7.  Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Authors:  Hiroki Sato; Ben W H Turnbull; Keisuke Fukaya; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

8.  Fused-Ring Formation by an Intramolecular "Cut-and-Sew" Reaction between Cyclobutanones and Alkynes.

Authors:  Lin Deng; Likun Jin; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

9.  Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors:  Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-11       Impact factor: 15.419

10.  Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy.

Authors:  Craig S Buxton; David C Blakemore; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336

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