Regio- and diastereoselective reactions of chiral secondary alkylcopper reagents with propargylic phosphates: preparation of chiral allenes

Skotnitzki, Juri; Kremsmair, Alexander; Keefer, Daniel; Schuppel, Franziska; de Bonneville, Brieuc Le Cacher; De Vivie-Riedle, Regina und Knochel, Paul (2020): Regio- and diastereoselective reactions of chiral secondary alkylcopper reagents with propargylic phosphates: preparation of chiral allenes. In: Chemical Science, Bd. 11, Nr. 20: S. 5328-5332

Abstract

The diastereoselective S(N)2 '-substitution of secondary alkylcopper reagents with propargylic phosphates enables the preparation of stereodefined alkylallenes. By using enantiomerically enriched alkylcopper reagents and enantioenriched propargylic phosphates as electrophiles anti-S(N)2 '-substitutions were performend leading to alpha-chiral allenes in good yields with excellent regioselectivity and retention of configuration. DFT-calculations were performed to rationalize the structure of these alkylcopper reagents in various solvents, emphasizing their configurational stability in THF.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 2041-6520
• Sprache: Englisch