title: Controlling olefin geometry with Pd catalysis: selective formation of Z-olefins from both E- and Z-allylic carbonates.
abstract: The palladium-catalyzed formation of Z-olefins from allylic carbonates and a variety of protected dialkyl aminomalonates is reported. The reaction is selective for the Z-isomer, and either acetyl, Boc, or formyl protecting groups are tolerated. The Z-olefin product can be formed regardless of whether the E- or Z-allylic carbonate is used as starting material.
authors.affiliation: Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. dietrich_steinhuebel@merck.com
authors.forename: Dietrich
authors.initials: D
authors.lastname: Steinhuebel
authors.forename: Michael
authors.initials: M
authors.lastname: Palucki
authors.forename: Ian W
authors.initials: IW
authors.lastname: Davies
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012997:Solvents
chemical_list: D000475:Alkenes; D002254:Carbonates; D012997:Solvents; D010165:Palladium