title: Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone: a new ambident diene.
abstract: D-A cycloadditions of 3,5-dibromo-2-pyrone were investigated with a series of electronically and sterically distinct dienophiles. Our results showed that it is a highly potent ambident diene, being more reactive and stereoselective than monobromo-2-pyrones, and thus capable of generating a variety of bicycloadducts in much higher chemical yields and endo/exo ratios than monobromo-2-pyrones. Another interesting feature of this study is that the two bromine groups on the cycloadducts could be independently manipulated to produce other synthetically useful bicyclolactones.
authors.affiliation: Department of Chemistry, Hanyang University, Seoul 131-791, Korea. ccho@hanyang.ac.kr
authors.forename: Cheon-Gyu
authors.initials: CG
authors.lastname: Cho
authors.forename: Yong-Woo
authors.initials: YW
authors.lastname: Kim
authors.forename: Young-Kwan
authors.initials: YK
authors.lastname: Lim
authors.forename: Jung-Sang
authors.initials: JS
authors.lastname: Park
authors.forename: Haiwon
authors.initials: H
authors.lastname: Lee
authors.forename: Sangman
authors.initials: S
authors.lastname: Koo
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D002762:Cholecalciferol / Q000031:analogs & derivatives; D018360:Crystallography, X-Ray; D003500:Cyclization; D011753:Pyrones / Q000737:chemistry
chemical_list: C450850:3,5-dibromo-2-pyrone; D000466:Alkadienes; D011753:Pyrones; D002762:Cholecalciferol