title: (4+1) vs (4+2): Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C-C Activation.
abstract: Herein we describe a rhodium-catalyzed (4+1) cyclization between cyclobutanones and allenes, which provides a distinct [4.2.1]-bicyclic skeleton containing two quaternary carbon centers. The reaction involves C-C activation of cyclobutanones and employs allenes as a one-carbon unit. A variety of functional groups can be tolerated, and a diverse range of polycyclic scaffolds can be accessed. Excellent enantioselectivity can be obtained, which is enabled by a TADDOL-derived phosphoramidite ligand. The bridged bicyclic products can be further functionalized or derivatized though simple transformations.
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Xuan
authors.initials: X
authors.lastname: Zhou
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Guangbin
authors.initials: G
authors.lastname: Dong
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D001381:Azepines / Q000737:chemistry; D002074:Butanones / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D000475:Alkenes; D001381:Azepines; D002074:Butanones; C025947:propadiene; D012238:Rhodium