Palladium-catalyzed highly diastereoselective cyclic carbopalladation-carbonylative esterification tandem reaction of iododienes and iodoarylalkenes.
[formula: see text] Pd-catalyzed reaction of iododienes and iodoarylalkenes represented by 1, 8, and 10 under 1 atm of CO and a small amount of O2 in the presence of a base, e.g., NEt3, as well as MeOH and H2O in DMF can undergo a highly diastereoselective cyclic carbopalladation-carbonylative esterification tandem process (Type II C-Pd process) to give in high yields the corresponding ester-containing cyclization products, e.g., 2, 9, and 11, in as high as 98% diastereoselectivity.
Copéret
C
C
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Negishi
E
E
D000475:Alkenes / Q000138:chemical synthesis*; D017607:Aluminum Compounds; D002384:Catalysis; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis; D007202:Indicators and Reagents; D007462:Iodobenzenes / Q000138:chemical synthesis*; D018020:Lithium Compounds; D010165:Palladium / Q000737:chemistry*; D019163:Reducing Agents; D013237:Stereoisomerism
D000475:Alkenes; D017607:Aluminum Compounds; D004952:Esters; D007202:Indicators and Reagents; D007462:Iodobenzenes; D018020:Lithium Compounds; D019163:Reducing Agents; D010165:Palladium; C042073:lithium aluminum hydride