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Enantioselective N-Heterocyclic Carbene Catalyzed Cyclopentene Synthesis via the β-Azolium Ylide. 2018

Lydia Scott, and Yuji Nakano, and Changhe Zhang, and David W Lupton
School of Chemistry, Monash University, Clayton, 3800, Victoria, Australia.

Herein we report the cycloisomerization of electron-poor 1,5-dienes via the β-azolium ylide to give enantioenriched cyclopentenes. The reaction is mediated by a chiral N-heterocyclic carbene (NHC) catalyst, exploits readily available substrates, has good generality (17 examples), and displays excellent enantioselectivity (mostly >94:6). Studies demonstrating the viability of a related dynamic kinetic resolution are reported, as are those with alternate tethers and derivatizations.

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