title: Sequential asymmetric catalysis in Michael-Michael-Michael-aldol reactions: merging organocatalysis with photoredox catalysis in a one-pot enantioselective synthesis of highly functionalized decalines bearing a quaternary carbon stereocenter.
abstract: An expedited method has been developed for the enantioselective synthesis of highly functionalized decaline systems containing seven contiguous stereogenic centers with high enantioselectivities (>99% ee). The one-pot methodology comprises a cascade of organocatalytic double Michael-photocatalyzed Michael-aldol reactions of ethyl 2-bromo-6-formylhex-2-enoate, β-alkyl-α,β-unsaturated aldehydes, and α-alkyl-α,β-unsaturated aldehydes. The structure and absolute configuration of an appropriate product were confirmed by X-ray analysis.
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University , Chia-Yi, 621, Taiwan, R.O.C., and Instrumentation Center, National Taiwan University , Taipei, 106, Taiwan, R.O.C.
authors.forename: Bor-Cherng
authors.initials: BC
authors.lastname: Hong
authors.forename: Cheng-Wei
authors.initials: CW
authors.lastname: Lin
authors.forename: Wei-Kai
authors.initials: WK
authors.lastname: Liao
authors.forename: Gene-Hsiang
authors.initials: GH
authors.lastname: Lee
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D002244:Carbon