Controlling olefin geometry with Pd catalysis: selective formation of Z-olefins from both E- and Z-allylic carbonates.
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.
Steinhuebel
Dietrich
D
Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. dietrich_steinhuebel@merck.com
Palucki
Michael
M
Davies
Ian W
IW
D000475:Alkenes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012997:Solvents
D000475:Alkenes; D002254:Carbonates; D012997:Solvents; D010165:Palladium