title: Divergent Method to trans-5-Hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-Epiquinamide and (+)-Swainsonine.
abstract: An efficient diastereoselective approach to access trans-5-hydroxy-6-alkynyl/alkenyl-2-piperidinones has been developed through nucleophilic addition of α-chiral aldimines using alkynyl/alkenyl Grignard reagents. The diastereoselectivity of alkenyl in C-6 position of 2-piperidinone was controlled by α-alkoxy substitution, while the alkynyl was controlled by the coordination of the α-alkoxy substitution and stereochemistry of sulfinamide. The utility of this straightforward cascade process is demonstrated by the asymmetric synthesis of the (-)-epiquinamide and (+)-swainsonine.
authors.affiliation: †School of Pharmacy, Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, 220 Handan Road, Shanghai 200433, China.|‡College of Science, Northwest Agriculture and Forestry University, Shaanxi Yangling, 712100, China.
authors.forename: Chang-Mei
authors.initials: CM
authors.lastname: Si
authors.affiliation: †School of Pharmacy, Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, 220 Handan Road, Shanghai 200433, China.|‡College of Science, Northwest Agriculture and Forestry University, Shaanxi Yangling, 712100, China.
authors.forename: Zhuo-Ya
authors.initials: ZY
authors.lastname: Mao
authors.affiliation: §Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Han-Qing
authors.initials: HQ
authors.lastname: Dong
authors.affiliation: ‡College of Science, Northwest Agriculture and Forestry University, Shaanxi Yangling, 712100, China.
authors.forename: Zhen-Ting
authors.initials: ZT
authors.lastname: Du
authors.affiliation: †School of Pharmacy, Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, 220 Handan Road, Shanghai 200433, China.
authors.forename: Bang-Guo
authors.initials: BG
authors.lastname: Wei
authors.affiliation: †School of Pharmacy, Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, 220 Handan Road, Shanghai 200433, China.|§Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010881:Piperidones / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D000480:Alkynes; D010881:Piperidones; D011807:Quinolizines; C481035:epiquinamide; D017026:Swainsonine