title: Metal-free metathesis reaction of C-chiral allylic sulfilimines with aryl isocyanates: construction of chiral nonracemic allylic isocyanates.
abstract: We report the facile and efficient metal-free metathesis reaction of C-chiral allylic sulfilimines with aryl isocyanates. This process facilitates the room temperature construction of an array of chiral nonracemic allylic isocyanates, which are versatile intermediates for the construction of unsymmetrical ureas, carbamates, thiocarbamates and amides. Furthermore, the sulfilimine/isocyanate metathesis reaction with 4,4'-methylene diphenyl diisocyanate (4,4'-MDI) circumvents harsh reaction conditions and/or hazardous reagents employed with more classical methods for the preparation of this important functional group.
authors.affiliation: Department of Chemistry, Queen's University , Kingston, Ontario K7L 3N6, Canada.
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Grange
authors.forename: P Andrew
authors.initials: PA
authors.lastname: Evans
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D006841:Hydrocarbons, Aromatic; D007097:Imines; D017953:Isocyanates; C491149:allyl isocyanate; C586946:sulfilimine