title: Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3-Chlorochalcogenation of Cyclopropyl Carbaldehydes.
abstract: meso-Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3-chlorochalcogenated products. The transformation is achieved by a merged iminium-enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo- and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).
authors.affiliation: Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Wallbaum
authors.affiliation: Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Lennart K B
authors.initials: LK
authors.lastname: Garve
authors.affiliation: Institute of Inorganic and Analytical Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Peter G
authors.initials: PG
authors.lastname: Jones
authors.affiliation: Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
authors.forename: Daniel B
authors.initials: DB
authors.lastname: Werz
keywords: 1,3-bisfunctionalization; cyclopropane; enantioselectivity; organocatalysis; sulfur