Enantioselective N‐Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium |
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| Authors: | Rachel M. Gillard Jared E. M. Fernando Prof. David W. Lupton |
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| Affiliation: | School of Chemistry, Monash University, Clayton, Victoria, Australia |
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| Abstract: | Herein we report the enantioselective N‐heterocyclic carbene catalyzed (4+2) annulation of the dienyl acyl azolium with enolates. The reaction exploits readily accessible acyl fluorides and TMS enol ethers to give a range of highly enantio‐ and diastereo‐enriched cyclohexenes (most >97:3 er and >20:1 dr). The reaction was found to require high nucleophilicity NHC catalysts with mechanistic studies supporting a stepwise 1,6‐addition/β‐lactonization. |
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| Keywords: | 1,6-addition dienyl acyl azolium enantioselective catalysis N-heterocyclic carbene β -lactonization |
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