title: Direct catalytic asymmetric synthesis of N-heterocycles from commodity acid chlorides by employing α,β-unsaturated acylammonium salts.
abstract: Taming the beast, asymmetrically: Modulation of the reactivity of acid chlorides, using cinchona alkaloid catalysts, results in chiral α,β-unsaturated acylammoniums, which react with nucleophiles enantioselectively to give pyrrolidinones, piperid-2-ones, and dihydropyridinones. This nucleophile-catalyzed Michael/proton transfer/lactamization or lactonization organocascade leads to chiral intermediates previously employed for the synthesis of bioactive pharmaceuticals.
authors.affiliation: Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842 (USA).
authors.forename: Sreekumar
authors.initials: S
authors.lastname: Vellalath
authors.forename: Khoi N
authors.initials: KN
authors.lastname: Van
authors.forename: Daniel
authors.initials: D
authors.lastname: Romo
keywords: enols; heterocycles; natural products; organocatalysis; synthetic methods