Literature DB >> 16104725

Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: cocatalyst effects and evidence for an enamine intermediate.

Timothy J Peelen1, Yonggui Chi, Samuel H Gellman.   

Abstract

An enantioselective intermolecular Michael addition of aldehydes to enones catalyzed by imidazolidinones has been achieved. Chemoselectivity (Michael addition vs aldol) can be controlled through judicious choice of hydrogen-bond-donating cocatalysts. The optimal imidazolidinone/hydrogen-bond-donor pair affords Michael addition products in excess of 90% ee. Furthermore, we have isolated and characterized an enamine intermediate and demonstrated its efficacy as a nucleophile in the observed Michael addition reactions.

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Year:  2005        PMID： 16104725     DOI： 10.1021/ja0532584

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Authors:  Claire M Filloux; Stephen P Lathrop; Tomislav Rovis
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-16       Impact factor: 11.205

2.  Enantioselective route to platensimycin: an intramolecular Robinson annulation approach.

Authors:  Pingfan Li; Joshua N Payette; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2007-07-14       Impact factor: 15.419

3.  Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

Authors:  Yonggui Chi; Li Guo; Nathan A Kopf; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2008-04-04       Impact factor: 15.419

4.  Concise synthesis of ricciocarpin A and discovery of a more potent analogue.

Authors:  Anna Michrowska; Benjamin List
Journal:  Nat Chem       Date:  2009-05-22       Impact factor: 24.427

5.  Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.

Authors:  Kun Huang; Francisco G Merced; Margarita Ortiz-Marciales; Héctor J Meléndez; Wildeliz Correa; Melvin De Jesús
Journal:  J Org Chem       Date:  2008-05-01       Impact factor: 4.354

6.  Amino acid salt catalyzed intramolecular Robinson annulation.

Authors:  Pingfan Li; Hisashi Yamamoto
Journal:  Chem Commun (Camb)       Date:  2009-08-04       Impact factor: 6.222

7.  A quantitative approach to nucleophilic organocatalysis.

Authors:  Herbert Mayr; Sami Lakhdar; Biplab Maji; Armin R Ofial
Journal:  Beilstein J Org Chem       Date:  2012-09-05       Impact factor: 2.883

8.  Fullerene C60 promoted photochemical hydroamination reactions of an electron deficient alkyne with trimethylsilyl group containing tertiary N-alkylbenzylamines.

Authors:  Suk Hyun Lim; Hannara Jang; Dae Won Cho
Journal:  RSC Adv       Date:  2021-02-03       Impact factor: 3.361

9.  (2S,4R)-2-[(1R)-1-(4-Bromo-phen-yl)-2-nitro-eth-yl]-4-ethyl-cyclo-hexa-none.

Authors:  Chi-Xiao Zhang; Yan-Peng Zhang; Ai-Bao Xia
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-01-19

10.  A case study of proton shuttling in palladium catalysis.

Authors:  Julien Monot; Paul Brunel; Christos E Kefalidis; Noel Ángel Espinosa-Jalapa; Laurent Maron; Blanca Martin-Vaca; Didier Bourissou
Journal:  Chem Sci       Date:  2015-12-07       Impact factor: 9.825
  10 in total

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