Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand.

Autor: Fulton TJ; Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, Pasadena, California 91125, United States of America., Wu B; Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, Pasadena, California 91125, United States of America., Alexy EJ; Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, Pasadena, California 91125, United States of America., Zhang H; Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States of America., Stoltz BM; Warren and Katharine Schlinger Laboratory of Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, Pasadena, California 91125, United States of America.
Jazyk: angličtina
Zdroj: Tetrahedron [Tetrahedron] 2019 Aug 02; Vol. 75 (31), pp. 4104-4109. Date of Electronic Publication: 2019 Jun 01.
DOI: 10.1016/j.tet.2019.05.065
Abstrakt: A unique example of Pd-catalyzed decarboxylative dehydrogenation of fully substituted N -acyl allyl enol carbonates is enabled by a new electron deficient phosphinooxazoline (PHOX) ligand. The reaction proceeds from the Z -enol carbonate to provide dehydrogenation products exclusively in high E/Z selectivity, while the E -enol carbonate provides the α-allylation product with only minor dehydrogenation. The reaction proceeds with a broad scope of ( Z )-enol carbonates derived from N -acyl indoles to furnish acyclic formal α,β-unsaturated ester equivalents.
Databáze: MEDLINE
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