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ChemInform Abstract: Enantioselective All-Carbon (4 + 2) Annulation by N-Heterocyclic Carbene Catalysis.
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The enantioselective vinylogous Michael/aldol cascade is an underdeveloped approach to cyclohexenes. Herein we describe a highly enantio- (most ≥98:2 er) and diastereoselective (all ≥15:1 dr) N heterocyclic carbene catalyzed cycloisomerization of acyclic ester dienolates to cyclohexyl β-lactones. Derivatizations avail various cyclohexenes bearing 4-contiguous stereogenic centers while mechanistic studies support olefin isomerization prior to cyclization.