title: Chemoselective Intramolecular Carbonyl Ylide Formation through Electronically Differentiated Malonate Diesters.
abstract: A method for chemoselective carbonyl ylide formation utilizing the Rh(II) catalyzed decomposition of electronically differentiated diazo malonates is disclosed. Treatment of ethyl, trifluoro ethyl diazo malonate with a Rh(II) catalyst selectively forms a carbonyl ylide from the relatively electron rich ethyl ester. This carbonyl ylide can be trapped by various alkynes giving highly functionalized oxabicyclic compounds in a chemo-, regio-, and diastereoselective fashion.
authors.affiliation: Department of Chemistry and Biochemistry, Baylor University , Waco, Texas 76798, United States.
authors.forename: Mina C
authors.initials: MC
authors.lastname: Nakhla
authors.affiliation: Department of Chemistry and Biochemistry, Baylor University , Waco, Texas 76798, United States.
authors.forename: Che-Wah
authors.initials: CW
authors.lastname: Lee
authors.affiliation: Department of Chemistry and Biochemistry, Baylor University , Waco, Texas 76798, United States.
authors.forename: John L
authors.initials: JL
authors.lastname: Wood
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004952:Esters; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D004952:Esters; D008314:Malonates; C030290:malonic acid; D012238:Rhodium