Unexpected Regioselectivity Switch: Organophosphine-Triggered Reactions of Cyclopropene-1,1-dicarboxylates with Aldehydes
2013-07-05T00:00:00Z (GMT) by
With tris(4-methoxyphenyl)phosphine as the nucleophilic reagent, the readily available cyclopropene-1,1-dicarboxylates undergo a ring-opening reaction to generate a Wittig-type intermediate, which would react with aromatic aldehydes to yield (E)-5-aryl-2-(methoxycarbonyl)-2,4-pentadienoates. It is interesting to observe that the regioselectivity of the ring-opening reaction is switched.
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