doi: 10.1021/ol052222d.
Palladium-catalyzed enantioselective conjugate addition of arylboronic acids
Affiliations
- PMID: 16268565
- DOI: 10.1021/ol052222d
Item in Clipboard
Palladium-catalyzed enantioselective conjugate addition of arylboronic acids
Org Lett.
.
Abstract
[reaction: see text] The first asymmetric palladium-catalyzed conjugate addition of arylboronic acids to alpha,beta-unsaturated aldehydes, ketones, and esters is described. For cyclic substrates, excellent chemo-, regio-, and enantioselectivities are achieved when a Pd(O2CCF3)2/DuPHOS catalyst is applied.
Similar articles
-
Pd(II)-bipyridine catalyzed conjugate addition of arylboronic acid to alpha,beta-unsaturated carbonyl compounds.J Org Chem. 2005 Nov 11;70(23):9651-3. doi: 10.1021/jo051561h. J Org Chem. 2005. PMID: 16268654
-
Rhodium-catalyzed 1,4-addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds: large accelerating effects of bases and ligands.J Org Chem. 2003 Jul 25;68(15):6000-4. doi: 10.1021/jo0207067. J Org Chem. 2003. PMID: 12868939
-
Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-gamma-lycorane.Org Lett. 2005 Sep 15;7(19):4285-8. doi: 10.1021/ol051795n. Org Lett. 2005. PMID: 16146408
-
Preparation of C2-symmetric bicyclo[2.2.2]octa-2,5-diene ligands and their use for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids.J Org Chem. 2005 Apr 1;70(7):2503-8. doi: 10.1021/jo047831y. J Org Chem. 2005. PMID: 15787536
-
Recent advances in palladium-catalysed asymmetric 1,4-additions of arylboronic acids to conjugated enones and chromones.Beilstein J Org Chem. 2021 May 10;17:1048-1085. doi: 10.3762/bjoc.17.84. eCollection 2021. Beilstein J Org Chem. 2021. PMID: 34093877 Free PMC article. Review.
Cited by
-
Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.Top Curr Chem (Cham). 2021 Jan 5;379(1):3. doi: 10.1007/s41061-020-00316-4. Top Curr Chem (Cham). 2021. PMID: 33398642 Review.
-
Phosphinite- and phosphite-based Type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines.Tetrahedron Lett. 2007 Jul 23;48(30):5283-5288. doi: 10.1016/j.tetlet.2007.05.119. Tetrahedron Lett. 2007. PMID: 18648490 Free PMC article.
-
Palladium(ii)-catalyzed γ-selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids.Chem Sci. 2018 Sep 6;9(44):8363-8368. doi: 10.1039/c8sc03081b. eCollection 2018 Nov 28. Chem Sci. 2018. PMID: 30542583 Free PMC article.
-
Stereoselectivity Predictions for the Pd-Catalyzed 1,4-Conjugate Addition Using Quantum-Guided Molecular Mechanics.J Org Chem. 2021 Apr 16;86(8):5660-5667. doi: 10.1021/acs.joc.1c00136. Epub 2021 Mar 26. J Org Chem. 2021. PMID: 33769065 Free PMC article.
-
Protodepalladation as a Strategic Elementary Step in Catalysis.Synthesis (Stuttg). 2018 Dec;50(24):4699-4714. doi: 10.1055/s-0037-1611064. Epub 2018 Oct 29. Synthesis (Stuttg). 2018. PMID: 31105348 Free PMC article.
LinkOut - more resources
Full Text Sources
