title: An Asymmetric Vinylogous Michael Cascade of Silyl Glyoximide, Vinyl Grignard, and Nitroalkenes via Long Range Stereoinduction.
abstract: A diastereoselective auxiliary-mediated vinylation/[1,2]-Brook rearrangement/vinylogous Michael cascade of silyl glyoximide, vinylmagnesium bromide, and nitroalkenes is described. The reaction occurs with complete regio- and diastereocontrol in good yield. The diastereoselectivity is induced by a rare instance of 1,7-chirality transfer that is hypothesized to arise from a trans-multihetero-decalin transition state.
authors.affiliation: Department of Chemistry and Physics, Florida Gulf Coast University , Fort Myers, Florida 33965, United States.
authors.forename: Gregory R
authors.initials: GR
authors.lastname: Boyce
authors.affiliation: Department of Chemistry, University of North Carolina , Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013453:Sulfonylurea Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D009574:Nitro Compounds; D013453:Sulfonylurea Compounds; D014753:Vinyl Compounds; C032160:glyoxamide
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