title: One-pot formation of chiral polysubstituted 3,4-dihydropyrans via a novel organocatalytic domino sequence involving alkynal self-condensation.
abstract: The self-condensation of alkynals was for the first time implemented under mild organocatalytic conditions and was successfully linked with a domino organocatalytic inverse-electron-demand oxa-Diels-Alder reaction, which led to the development of a facile one-pot method to produce a wide variety of polysubstituted chiral 3,4-dihydropyrans with good to high yields and diastereoselectivities and high enantioselectivities. The unprecedented alkynal self-condensation was revealed to pass through secondary amine-catalyzed C-C triple bond hydration and subsequent aldol condensation.
authors.affiliation: Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Li-Jin
authors.initials: LJ
authors.lastname: Dong
authors.forename: Tian-Tian
authors.initials: TT
authors.lastname: Fan
authors.forename: Chao
authors.initials: C
authors.lastname: Wang
authors.forename: Jian
authors.initials: J
authors.lastname: Sun
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000480:Alkynes; D011714:Pyrans