title: Lewis acid mediated (3 + 2) cycloadditions of donor-acceptor cyclopropanes with heterocumulenes.
abstract: Isocyanates, isothiocyanates, and carbodiimides are effective substrates in (3 + 2) cycloadditions with donor-acceptor cyclopropanes for the synthesis of five-membered heterocycles. These reactions exhibit a broad substrate scope, high yields, and well-defined chemoselectivity. Discussed herein are the implications of Lewis acid choice on the stereochemical outcome and the reaction mechanism.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 101-20, Pasadena, California 91125, USA.
authors.forename: Alexander F G
authors.initials: AF
authors.lastname: Goldberg
authors.forename: Nicholas R
authors.initials: NR
authors.lastname: O'Connor
authors.forename: Robert A
authors.initials: RA
authors.lastname: Craig
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D017953:Isocyanates; D058116:Lewis Acids; D011090:Polyenes