title: One-pot construction of aza- or oxa-bridged benzocycloheptanes from readily available 2,3-allenyl malonates or 2,3-allenols and o-iodobenzaldehyde or imine.
abstract: A Pd(OAc)(2)-catalyzed reaction of 2,3-alkadienyl malonates or 2,3-allenols with o-iodobenzaldehyde or its N-tosyl imine occurred smoothly in MeCN at 80 °C to form the oxa- or aza-bridged benzocycloheptane derivatives with important biological potential. With the optically active 2,3-allenols, the absolute configurations of all the three chiral centers have been conveniently established.
authors.affiliation: Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China.
authors.forename: Qiankun
authors.initials: Q
authors.lastname: Li
authors.forename: Xinpeng
authors.initials: X
authors.lastname: Jiang
authors.forename: Chunling
authors.initials: C
authors.lastname: Fu
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
chemical_list: D000466:Alkadienes; D001372:Aza Compounds; D001547:Benzaldehydes; D003508:Cycloheptanes; D006572:Heterocyclic Compounds, Bridged-Ring; D006847:Hydrocarbons, Iodinated; D007097:Imines; D008314:Malonates; C025947:propadiene; D010165:Palladium