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Competitive [2,3]- and [1,2]-Oxonium Ylide Rearrangements. Concerted or Stepwise?

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posted on 06.04.2012, 00:00 authored by Deana M. Jaber, Ryan N. Burgin, Matthew Helper, Peter Y. Zavalij, Michael P. Doyle
The axial–equatorial conformational isomer distribution of the reactant diazoacetoacetate or its metal carbene intermediate is reflected in Rh(II) catalyzed oxonium ylide forming reactions of 3-(trans-2-arylvinyl)tetrahydropyranone-5-diazoacetoacetates that afford diastereoisomeric products for both the symmetry-allowed [2,3]- and the formally symmetry-forbidden [1,2]-oxonium ylide rearrangements.