A unique rhodium-catalyzed rearrangement process: isomerization of an alkyne to a 1,3-diene with concomitant migration of a formyl group. An expeditious route to dienals from readily available 4-alkynals
In CH2Cl2, [Rh(BINAP)]BF4 catalyzes the isomerization of 4-alkynals to dienals with excellent regio- and stereoselectivity; this new process compares favorably with previously reported methods for the synthesis of this class of compounds; a possible pathway for this unusual rearrangement is provided.
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