Rh-catalyzed formation of dioxolanes from alpha-alkyl diazoesters: diastereoselective cycloadditions of carbonyl ylides with selectivity over beta-hydride elimination

The Journal of Organic Chemistry
Andrew DeAngelisJoseph M Fox

Abstract

Described here is a diastereoselective Rh-catalyzed method for the preparation of dioxolanes from alpha-alkyl-alpha-diazoesters. This represents the first general method for generating carbonyl ylides from alpha-diazoesters that possess beta-hydrogens, as such diazo compounds typically give rise to alkenes via beta-hydride elimination. Subsequent cycloaddition with aromatic aldehydes gives tetrasubstituted dioxolanes with unusually high diastereoselectivity. A model is set forth to explain the diastereoselectivity of the cycloaddition.

References

Mar 27, 2001·Organic Letters·M P DoyleD J Timmons
Apr 19, 1996·The Journal of Organic Chemistry·Douglass F. TaberJohn M. Geremia
Feb 19, 2002·Chemical Reviews·Michael P. Doyle, David C. Forbes

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Citations

Jan 27, 2011·Journal of the American Chemical Society·Andrew DeAngelisJoseph M Fox
Jan 9, 2009·Journal of the American Chemical Society·Andrew DeAngelisJoseph M Fox
May 28, 2009·Journal of the American Chemical Society·Andrew DeAngelisJoseph M Fox
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Aug 5, 2015·Organic Letters·Robert PanishJoseph M Fox
Aug 29, 2009·Organic Letters·Timothy M GreggJohn R Frost
May 19, 2021·Chemistry : a European Journal·Yasunori TodaHiroyuki Suga
Jan 5, 2013·Organic Letters·Changming Qin, Huw M L Davies

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