title: TiCl4-promoted tandem carbonyl or imine addition and Friedel-Crafts cyclization: synthesis of benzo-fused oxabicyclooctanes and nonanes.
abstract: A new and convenient synthesis of benzo-fused 8-oxabicyclo[3.2.1]octane and 9-oxabicyclo[4.2.1]nonane derivatives are described. The reaction involved a TiCl(4)-mediated tandem carbonyl or imine addition followed by a Friedel-Crafts cyclization to provide these functionalized derivatives in good to excellent yields and high diastereoselectivity.
authors.affiliation: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA. akghosh@purdue.edu
authors.forename: Arun K
authors.initials: AK
authors.lastname: Ghosh
authors.forename: Cuthbert D
authors.initials: CD
authors.lastname: Martyr
authors.forename: Chun-Xiao
authors.initials: CX
authors.lastname: Xu
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D000473:Alkanes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003516:Cycloparaffins; D005663:Furans; C025096:titanium tetrachloride; D014025:Titanium; C017573:nonane