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Phosphine-Catalyzed Annulation Reactions of 2‑Butynoate and α‑Keto Esters: Synthesis of Cyclopentene Derivatives

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posted on 03.10.2014, 00:00 by Curren T. Mbofana, Scott J. Miller
We have developed phosphine-catalyzed annulation reactions for the synthesis of highly substituted cyclopentene derivatives from 2-alkynoate and α-keto esters. These transformations involve carbon–carbon bond cleavage of α-keto esters. Preliminary mechanistic studies suggest that, in addition to facilitating carbon–carbon bond formation, the phosphine catalyst plays a role in promoting methanolysis.