title: Synergistic Diazo-OH Insertion/Conia-Ene Cascade Catalysis for the Stereoselective Synthesis of γ-Butyrolactones and Tetrahydrofurans.
abstract: A novel and highly efficient diazo-OH insertion/Conia-ene cascade reaction of readily available homopropargylic acids and alcohols with diazo carbonyl compounds is described. The cascade reaction involves a synergistic Rh/Ag/Au catalyst cocktail and proceeds instantly with a variety of substituted diazo compounds and acids/alcohols to provide functionalized γ-butyrolactones and tetrahydrofurans with complete regio- and stereoselectivity. The unprecedented rate-enhancement, complete stereoselectivity, and the enabling of new Conia-ene cyclizations suggest a concerted [4+1]-cycloaddition reaction pathway under synergistic (Rh/Ag/Au)-catalysis conditions.
authors.affiliation: Department of Chemistry and Biochemistry, and, Institute of Natural Products Applications and Research Technologies, University of Oklahoma, 101 Stephenson Parkway, Norman, OK, 73071, USA.
authors.forename: Arianne C
authors.initials: AC
authors.lastname: Hunter
authors.affiliation: Department of Chemistry and Biochemistry, and, Institute of Natural Products Applications and Research Technologies, University of Oklahoma, 101 Stephenson Parkway, Norman, OK, 73071, USA.
authors.forename: Steven C
authors.initials: SC
authors.lastname: Schlitzer
authors.affiliation: Department of Chemistry and Biochemistry, and, Institute of Natural Products Applications and Research Technologies, University of Oklahoma, 101 Stephenson Parkway, Norman, OK, 73071, USA. isharma@ou.edu.
authors.forename: Indrajeet
authors.identifier: http://orcid.org/0000-0002-0707-0621
authors.initials: I
authors.lastname: Sharma
keywords: O−H insertion; cascade reactions; conia-ene; diazo compounds; synergistic catalysis