The catalytic generation of chiral ester enolates or their equivalents with small organic catalysts for enantioselective carbon-carbon bond-forming reaction is a powerful strategy in reaction discovery and synthesis.We present herein highly enantioselective Diels-Alder reactions of chalcones and formylcyclopropanes catalyzed by chiral N-Heterocyclic Carbenes. We captured the challenging NHC-bounded enolate intermediates from formylcyclopropanes for new C-C bonding formation reactions, and significantly expands the scope of reverse-electron-demand hetero-Diels-Alder reactions that were previously limited to highly activated heteodienes. The reaction products could be easily transformed to optically pure multi-substituted cyclohexane derivatives.

Highly enantioselective Diels-Alder reactions of chalcones and formylcyclopropanes catalyzed by chiral N-heterocyclic carbenes

243rd National Meeting (2012)

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