title: A general, scalable, organocatalytic nitro-Michael addition to enones: enantioselective access to all-carbon quaternary stereocenters.
abstract: A tert-leucine-derived chiral diamine catalyzes the asymmetric Michael addition of nitromethane to five-, six-, and seven-membered β-substituted cyclic enones with excellent enantioselectivity, offering scalable, asymmetric access to all-carbon quaternary stereocenters. The reaction scope can be expanded to include linear acyclic enones, and excellent levels of enantioselectivity are also observed. Furthermore, this organocatalytic, asymmetric nitro-Michael reaction is amenable to multigram scale-up and applications in the construction of an eudesmane sesquiterpenoid skeleton.
authors.affiliation: †Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Gu
authors.affiliation: †Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
authors.forename: Yuanyuan
authors.initials: Y
authors.lastname: Dai
authors.affiliation: †Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
authors.forename: Tingting
authors.initials: T
authors.lastname: Guo
authors.affiliation: ‡Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Allegra
authors.initials: A
authors.lastname: Franchino
authors.affiliation: ‡Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
authors.affiliation: †Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
authors.forename: Jinxing
authors.initials: J
authors.lastname: Ye
mesh_terms: D002384:Catalysis; D003959:Diamines / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D045787:Sesquiterpenes, Eudesmane / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives
chemical_list: D003959:Diamines; D007659:Ketones; D009574:Nitro Compounds; D045787:Sesquiterpenes, Eudesmane; C089871:2-amino-3,3-dimethylbutanoic acid; D007930:Leucine; D014633:Valine