Functionalized chiral ionic liquid catalyzed enantioselective desymmetrizations of prochiral ketones via asymmetric Michael addition reaction
- PMID: 17975933
- DOI: 10.1021/jo7020357
Functionalized chiral ionic liquid catalyzed enantioselective desymmetrizations of prochiral ketones via asymmetric Michael addition reaction
Abstract
Functionalized chiral ionic liquids were found to be highly effective and reusable organocatalysts for asymmetric Michael additions of 4-substituted cyclohexanones. The desymmetrization reaction afforded the desired Michael adducts bearing three carbon stereocenters with up to 99% ee.
Similar articles
-
Chiral primary-secondary diamines catalyzed Michael-aldol-dehydration reaction between benzoylacetates and alpha,beta-unsaturated ketones: highly enantioselective synthesis of functionalized chiral cyclohexenones.Chemistry. 2009 Dec 14;15(48):13295-8. doi: 10.1002/chem.200901541. Chemistry. 2009. PMID: 19908264 No abstract available.
-
Functionalized chiral ionic liquids: a new type of asymmetric organocatalysts and nonclassical chiral ligands.Chem Asian J. 2009 Aug 3;4(8):1184-95. doi: 10.1002/asia.200900080. Chem Asian J. 2009. PMID: 19533671 Review.
-
Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones.Org Lett. 2007 Feb 1;9(3):413-5. doi: 10.1021/ol062718a. Org Lett. 2007. PMID: 17249775
-
Enantioselective Michael addition of alpha-substituted cyanoacetates to vinyl ketones catalyzed by bifunctional organocatalysts.Chemistry. 2007;13(1):319-27. doi: 10.1002/chem.200600796. Chemistry. 2007. PMID: 17039561
-
Emerging strategies in sustainable fine-chemical synthesis: asymmetric catalysis by metal nanoparticles.Dalton Trans. 2010 Sep 28;39(36):8391-402. doi: 10.1039/c002051f. Epub 2010 Apr 14. Dalton Trans. 2010. PMID: 20390200 Review.
Cited by
-
Coordinating Chiral Ionic Liquids: Design, Synthesis, and Application in Asymmetric Transfer Hydrogenation under Aqueous Conditions.European J Org Chem. 2015 Apr;2015(11):2374-2381. doi: 10.1002/ejoc.201403555. Epub 2015 Feb 20. European J Org Chem. 2015. PMID: 26279638 Free PMC article.
-
(2S,4S)-2-[(S,E)-2-Bromo-1-nitro-methyl-3-phenyl-all-yl]-4-methyl-cyclo-hexa-none.Acta Crystallogr Sect E Struct Rep Online. 2012 Apr 1;68(Pt 4):o1253. doi: 10.1107/S1600536812013098. Epub 2012 Mar 31. Acta Crystallogr Sect E Struct Rep Online. 2012. PMID: 22606184 Free PMC article.
-
Asymmetric Michael Addition Mediated by Chiral Ionic Liquids.Mini Rev Org Chem. 2018 Jun;15(3):236-245. doi: 10.2174/1570193X15666171211165344. Mini Rev Org Chem. 2018. PMID: 29861702 Free PMC article. Review.
-
(2S,4R)-2-[(1R)-1-(4-Bromo-phen-yl)-2-nitro-eth-yl]-4-ethyl-cyclo-hexa-none.Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 1;69(Pt 2):o263. doi: 10.1107/S1600536813001426. Epub 2013 Jan 19. Acta Crystallogr Sect E Struct Rep Online. 2013. PMID: 23424539 Free PMC article.
-
Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters.Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4899-903. doi: 10.1002/anie.201411924. Epub 2015 Feb 27. Angew Chem Int Ed Engl. 2015. PMID: 25727215 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources