Sc(OTf)₃-Catalyzed Addition of Bromomagnesium 2-Vinyloxy Ethoxide to Various Aldehydes Leading to Protected Aldol Products

Quinio, Pauline; Kohout, Laura; Sustac Roman, Daniela; Gaar, Jakob; Karaghiosoff, Konstantin und Knochel, Paul (2016): Sc(OTf)₃-Catalyzed Addition of Bromomagnesium 2-Vinyloxy Ethoxide to Various Aldehydes Leading to Protected Aldol Products. In: Synlett, Bd. 27, Nr. 11: S. 1715-1719

Abstract

The addition of bromomagnesium 2-vinyloxy ethoxide to various aldehydes in the presence of 10 mol% Sc(OTf)(3) provides a broad range of functionalized protected aldol compounds. The enantioselective preparation of these aldols can be achieved via a Swern oxidation-CBS reduction sequence. Use of the dioxolane derived from 2-bromocyclohexanone provides the expected aldol product as the anti diastereoisomer (dr >99:1).

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0936-5214
• Sprache: Englisch