title: Experimental and Computational Studies of the Diastereoselective Alkylations of 3-Substituted γ-Sultams.
abstract: We report that chiral 3-substituted γ-sultam α-carbanions undergo diastereoselective alkylation reactions with alkyl halides to predominantly produce trans-3,5-disubstituted γ-sultam products. Quantum mechanical calculations provided a stereoelectronic rationale for the observed diastereoselectivity.
authors.affiliation: Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: Benjamin P
authors.initials: BP
authors.lastname: Fauber
authors.affiliation: Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: Kyle
authors.initials: K
authors.lastname: Clagg
authors.affiliation: Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: Paul
authors.initials: P
authors.lastname: Gibbons
authors.affiliation: Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: Olivier
authors.initials: O
authors.lastname: René
mesh_terms: D000478:Alkylation; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D009282:Naphthalenesulfonates / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D009282:Naphthalenesulfonates; C016768:naphthosultone