Highly enantioselective ketone-ene reactions of trifluoropyruvate: significant counterion effect of the In(III)-pybox complex
- PMID: 19911807
- DOI: 10.1021/ol902507x
Highly enantioselective ketone-ene reactions of trifluoropyruvate: significant counterion effect of the In(III)-pybox complex
Abstract
A chiral indium(III)-pybox complex catalyzed asymmetric ketone-ene reaction of trifluoropyruvate is described. Both aromatic and aliphatic 1,1-disubstituted alkenes reacted smoothly to give the enantioenriched tertiary homoallylic alcohols in good to excellent yields (up to 99%) and with excellent enantioselectivities (up to 98% ee).
Similar articles
-
Highly enantioselective allylation of aldehydes catalyzed by indium(III)-PYBOX complex.Org Lett. 2005 Jan 6;7(1):159-61. doi: 10.1021/ol047711c. Org Lett. 2005. PMID: 15625002
-
Enantioselective allylation of ketones catalyzed by chiral In(III)-PYBOX complexes.Chem Commun (Camb). 2005 Sep 7;(33):4217-8. doi: 10.1039/b507768k. Epub 2005 Jul 25. Chem Commun (Camb). 2005. PMID: 16100608
-
Enantioselective allylation of aldehydes catalyzed by chiral indium(III) complexes immobilized in ionic liquids.Chem Commun (Camb). 2005 May 14;(18):2345-7. doi: 10.1039/b500086f. Epub 2005 Mar 15. Chem Commun (Camb). 2005. PMID: 15877123
-
Enantioselective synthesis of homoallylic alcohols via a chiral In(III)-PYBOX complex.Chem Commun (Camb). 2005 Feb 28;(8):1010-2. doi: 10.1039/b415550e. Epub 2005 Jan 5. Chem Commun (Camb). 2005. PMID: 15719099
-
Asymmetric carbonyl-ene reaction catalyzed by chiral N,N'-dioxide-nickel(II) complex: remarkably broad substrate scope.J Am Chem Soc. 2008 Nov 26;130(47):15770-1. doi: 10.1021/ja808023y. J Am Chem Soc. 2008. PMID: 18980310
Cited by
-
Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins.Org Lett. 2011 Nov 4;13(21):5754-7. doi: 10.1021/ol202329s. Epub 2011 Oct 11. Org Lett. 2011. PMID: 21992567 Free PMC article.
-
Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc.Beilstein J Org Chem. 2018 Mar 7;14:576-582. doi: 10.3762/bjoc.14.44. eCollection 2018. Beilstein J Org Chem. 2018. PMID: 29623119 Free PMC article.
-
Domino dehydration/intermolecular (enantioselective) ketone-ene reactions catalysed by a simple solid in batch and in flow.RSC Adv. 2024 Oct 18;14(45):32944-32957. doi: 10.1039/d4ra06449f. eCollection 2024 Oct 17. RSC Adv. 2024. PMID: 39429935 Free PMC article.
LinkOut - more resources
Full Text Sources