title: Enantioselective synthesis of highly functionalized phosphonate-substituted pyrans or dihydropyrans through asymmetric [4+2] cycloaddition of β,γ-unsaturated α-ketophosphonates with allenic esters.
abstract: Tell me which you want: catalytic asymmetric [4+2] cycloadditions of β,γ-unsaturated α-ketophosphonates with allenic esters catalyzed by organocatalysts derived from different cinchona alkaloids have been developed, affording phosphonate-substituted functionalized pyran and dihydropyran derivatives in excellent yields with high enantioselectivities under mild conditions. The choice of product is controlled by the hydrogen bonding characteristics of the chosen catalyst.
authors.affiliation: Key Laboratory for Advanced Materials, East China University of Science and Technology, Shanghai, China.
authors.forename: Cheng-Kui
authors.initials: CK
authors.lastname: Pei
authors.forename: Yu
authors.initials: Y
authors.lastname: Jiang
authors.forename: Yin
authors.initials: Y
authors.lastname: Wei
authors.forename: Min
authors.initials: M
authors.lastname: Shi
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D063065:Organophosphonates; D011714:Pyrans