Lewis acid-promoted hetero Diels-Alder cycloaddition of alpha-acetoxynitroso dienophiles

Organic Letters
Géraldine CalvetCyrille Kouklovsky

Abstract

[reaction: see text] alpha-Acetoxynitroso compound 3 has been prepared as a new stable, isolable, and reactive dienophile in nitroso Diels-Alder reactions. The yield of the [4 + 2] cycloaddition of alpha-acetoxynitroso dienophile with 1,3-dienes could be enhanced in the presence of 20 mol % Lewis acid. An unexpected retro hetero-Michael reaction from 26 was observed, leading to the cleavage of the N-O bond of the cycloadduct. This tandem nitroso Diels-Alder/retro hetero-Michael sequence has been used with cyclic and acyclic 1,3-dienes.

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Citations

Jul 13, 2005·Chemical Communications : Chem Comm·Hisashi Yamamoto, Norie Momiyama
Jan 18, 2011·Antioxidants & Redox Signaling·Jenna F DuMond, S Bruce King
Nov 27, 2015·Journal of the American Chemical Society·Biplab Maji, Hisashi Yamamoto
Jan 18, 2017·Chemical Communications : Chem Comm·Jun LiChun-Jiang Wang
Jul 4, 2015·Chemical Communications : Chem Comm·Erika Nakashima, Hisashi Yamamoto
Oct 15, 2005·Angewandte Chemie·Yuhei Yamamoto, Hisashi Yamamoto
Dec 6, 2005·Organic & Biomolecular Chemistry·Géraldine CalvetCyrille Kouklovsky
Feb 10, 2011·Chemistry : a European Journal·Guillaume Vincent, Cyrille Kouklovsky
Jan 16, 2016·Oxidative Medicine and Cellular Longevity·Mai E Shoman, Omar M Aly
Oct 15, 2013·Chemistry : a European Journal·Gilles GalvaniCyrille Kouklovsky
Mar 17, 2009·The Journal of Organic Chemistry·Paolo QuadrelliPierluigi Caramella
Mar 14, 2007·Organic Letters·Géraldine CalvetCyrille Kouklovsky
Oct 24, 2008·Chemical Reviews·Sébastien Reymond, Janine Cossy
Jul 27, 2006·Journal of the American Chemical Society·Xin ShaS Bruce King

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