title: Rhodium Carbenoid Initiated O-H Insertion/Aldol/Oxy-Cope Cascade for the Stereoselective Synthesis of Functionalized Oxacycles.
abstract: A novel diazo-cascade approach has been developed for the synthesis of nine-membered oxacycles utilizing readily accessible β-hydroxy vinyl ketones and vinyl diazo esters. The Rh(II)-catalyzed cascade reaction begins with carbene O-H insertion followed by an intramolecular aldol cyclization to provide a substituted tetrahydrofuran intermediate that undergoes an oxy-Cope rearrangement to provide functionalized nine-membered oxacycles with complete stereoselectivity.
authors.affiliation: Department of Chemistry and Biochemistry, and Institute of Natural Products Applications and Research Technologies University of Oklahoma , 101 Stephenson Parkway, Norman, Oklahoma 73071, United States.
authors.forename: Kiran
authors.initials: K
authors.lastname: Chinthapally
authors.affiliation: Department of Chemistry and Biochemistry, and Institute of Natural Products Applications and Research Technologies University of Oklahoma , 101 Stephenson Parkway, Norman, Oklahoma 73071, United States.
authors.forename: Nicholas P
authors.initials: NP
authors.lastname: Massaro
authors.affiliation: Department of Chemistry and Biochemistry, and Institute of Natural Products Applications and Research Technologies University of Oklahoma , 101 Stephenson Parkway, Norman, Oklahoma 73071, United States.
authors.forename: Indrajeet
authors.identifier: 0000-0002-0707-0621
authors.initials: I
authors.lastname: Sharma