Author(s): Ahmad Fakhruddin, Kesiny Phomkeona, Abdel-Moneim Abu-Elfotoh, Kazutaka Shibatomi and Seiji Iwasa
Page: [475 - 478] Pages: 4
* (Excluding Mailing and Handling)
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.
Keywords: Nitroso intermediate, hydrogen peroxide, ruthenium catalyst, iridium catalyst, hetero Diels-Alder reaction, 1, 2-oxazine
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