Ru(II)- and Ir(I) Catalyzed Hydrogen Peroxide Oxidation of Hydroxamic Acids and their Subsequent Hetero Diels-Alder Cycloadditions with Chiral N-Dienyl Lactams

Title: Ru(II)- and Ir(I) Catalyzed Hydrogen Peroxide Oxidation of Hydroxamic Acids and their Subsequent Hetero Diels-Alder Cycloadditions with Chiral N-Dienyl Lactams

Volume: 7 Issue: 6

Author(s): Ahmad Fakhruddin, Kesiny Phomkeona, Abdel-Moneim Abu-Elfotoh, Kazutaka Shibatomi and Seiji Iwasa

Affiliation:

Keywords: Nitroso intermediate, hydrogen peroxide, ruthenium catalyst, iridium catalyst, hetero Diels-Alder reaction, 1, 2-oxazine

Abstract: Asymmetric hetero Diels-Alder (HDA) reaction of highly reactive acyl nitroso intermediates are reported. Transient acyl nitroso compounds 2a-c are formed by Ru(II)- or Ir(I)-catalyzed hydrogen peroxide oxidation of hydroxamic acids 2a-c and are trapped in situ by the optically pure N-dienyl-L-pyroglutamates 1a-b to afford the corresponding diastereomeric adducts 3a-f and 4a-f up to 98% yield (70% de) and 72% de (70% yield) with complete regioselectivity at 0°C to room temperature.

Cite this article as:

Fakhruddin Ahmad, Phomkeona Kesiny, Abu-Elfotoh Abdel-Moneim, Shibatomi Kazutaka and Iwasa Seiji, Ru(II)- and Ir(I) Catalyzed Hydrogen Peroxide Oxidation of Hydroxamic Acids and their Subsequent Hetero Diels-Alder Cycloadditions with Chiral N-Dienyl Lactams, Letters in Organic Chemistry 2010; 7 (6) . https://dx.doi.org/10.2174/157017810791824955