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N-Heterocyclic Carbene-catalyzed Annulation Of α-cyano-1,4-diketones With Ynals.

Fedor Romanov‐Michailidis, C. Besnard, A. Alexakis
Published 2012 · Chemistry, Medicine

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In this paper, the first stereoselective annulation reaction between α-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.
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