title: Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactams to Dienones.
abstract: An asymmetric doubly vinylogous Michael addition (DVMA) of α,β-unsaturated γ-butyrolactams to sterically congested β-substituted cyclic dienones with high site-, diastereo-, and enantioselectivity has been achieved. An unprecedented DVMA/vinylogous Michael addition/isomerization cascade reaction affords chiral fused tricyclic γ-lactams with four newly formed stereocenters.
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, 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 Centre of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, 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: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, 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: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA (UK).
authors.forename: Allegra
authors.initials: A
authors.lastname: Franchino
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China).
authors.forename: Jie
authors.initials: J
authors.lastname: Fei
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China).
authors.forename: Chuncheng
authors.initials: C
authors.lastname: Zou
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA (UK). darren.dixon@chem.ox.ac.uk.
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
authors.affiliation: Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237 (China). yejx@ecust.edu.cn.
authors.forename: Jinxing
authors.initials: J
authors.lastname: Ye
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007659:Ketones / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007659:Ketones; D007769:Lactams
keywords: asymmetric catalysis; conjugation; cyclizations; nucleophilic addition; organocatalysis