Asymmetric Electrophilic α-Amination of Silyl Enol Ether Derivatives via the Nitrosocarbonyl Hetero-ene Reaction

Organic Letters
David SandovalJavier Read de Alaniz

Abstract

The first example of a general asymmetric nitrosocarbonyl hetero-ene reaction is described. The procedure uses a copper-catalyzed aerobic oxidation of a commercially available chiral nitrosocarbonyl precursor (EleNOr) and is operationally simple. The transformation is both high yielding and highly diastereoselective for a range of silyl enol ether derivatives. A variety of synthetically useful postfunctionalization reactions are presented along with a mechanistic rationale that can be used as a predictive model for future asymmetric reactions with nitrosocarbonyl intermediates.

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Citations

Feb 10, 2016·Journal of the American Chemical Society·Keisuke TokumasuTakashi Ohshima
Jun 29, 2016·Journal of the American Chemical Society·Veronica TonaNuno Maulide
Sep 13, 2016·The Journal of Organic Chemistry·Saghar NourianJohn P Toscano
Jan 21, 2017·Chemical Reviews·Misal Giuseppe Memeo, Paolo Quadrelli
Mar 14, 2017·Organic Letters·Mallu Kesava ReddyMahiuddin Baidya
Jan 27, 2016·Chemical Communications : Chem Comm·Isai RamakrishnaMahiuddin Baidya

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