Literature DB >> 16193126

Organocatalytic asymmetric alpha-bromination of aldehydes and ketones.

Søren Bertelsen1, Nis Halland, Stephan Bachmann, Mauro Marigo, Alan Braunton, Karl Anker Jørgensen.   

Abstract

The first organocatalytic enantioselective alpha-bromination of aldehydes and ketones is presented; a C2-symmetric diphenylpyrrolidine catalyst afforded the alpha-brominated aldehydes in good yields and up to 96% ee, while ketones were alpha-brominated by a C2-symmetric imidazolidine in up to 94% ee; furthermore, the organocatalytic enantioselective alpha-iodination of aldehydes is also demonstrated to proceed with up to 89% ee.

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Year:  2005        PMID: 16193126     DOI: 10.1039/b509366j

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


  6 in total

1.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

2.  Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Authors:  Jakub Saadi; Matsujiro Akakura; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

3.  Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines.

Authors:  Nathan W Polaske; Ramin Dubey; Gary S Nichol; Bogdan Olenyuk
Journal:  Tetrahedron Asymmetry       Date:  2009-12-11

4.  Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide.

Authors:  George Hutchinson; Carla Alamillo-Ferrer; Martín Fernández-Pascual; Jordi Burés
Journal:  J Org Chem       Date:  2022-05-26       Impact factor: 4.198

5.  Simple and regioselective bromination of 5,6-disubstituted-indan-1-ones with Br2 under acidic and basic conditions.

Authors:  Taeyoung Choi; Eunsook Ma
Journal:  Molecules       Date:  2007-01-29       Impact factor: 4.411

6.  Asymmetric intramolecular α-cyclopropanation of aldehydes using a donor/acceptor carbene mimetic.

Authors:  Chaosheng Luo; Zhen Wang; Yong Huang
Journal:  Nat Commun       Date:  2015-12-08       Impact factor: 14.919

  6 in total

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