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N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

Published in Organic Letters. 2012, vol. 14, no. 18, p. 4906-4909
Abstract 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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ROMANOV MICHAILIDIS, Fedor, BESNARD, Céline, ALEXAKIS, Alexandre. N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals. In: Organic Letters, 2012, vol. 14, n° 18, p. 4906-4909. doi: 10.1021/ol3022287 https://archive-ouverte.unige.ch/unige:23520

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Deposited on : 2012-10-22

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