title: Aminocatalytic asymmetric exo-Diels-Alder reaction with methiodide salts of Mannich bases and 2,4-dienals to construct chiral spirocycles.
abstract: An asymmetric exo-Diels-Alder reaction of α-methylene carbonyl compounds, generated in situ from stable methiodide salts of Mannich bases, with 2,4-dienals, has been developed through trienamine activation of a chiral secondary amine. A spectrum of spirocyclanes with high molecular complexity was efficiently constructed in moderate to excellent diastereo- and enantioselectivity.
authors: Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors: Shan-Jun
authors: SJ
authors: Zhang
authors: Jun
authors: J
authors: Zhang
authors: Qing-Qing
authors: QQ
authors: Zhou
authors: Lin
authors: L
authors: Dong
authors: Ying-Chun
authors: YC
authors: Chen
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001640:Bicuculline / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D008352:Mannich Bases / Q000737:chemistry*; D015394:Molecular Structure; D012492:Salts; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D008352:Mannich Bases; D012492:Salts; D013141:Spiro Compounds; C017069:bicuculline methiodide; D001640:Bicuculline