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  • Title: Enantioselective all-carbon (4+2) annulation by N-heterocyclic carbene catalysis.
    Author: Candish L, Levens A, Lupton DW.
    Journal: J Am Chem Soc; 2014 Oct 15; 136(41):14397-400. PubMed ID: 25252043.
    Abstract:
    The enantioselective vinylogous Michael/aldol cascade is an underdeveloped approach to cyclohexenes. Herein we describe a highly enantioselective (most ≥ 98:2 er) and diastereoselective (all ≥ 15:1 dr) N-heterocyclic carbene catalyzed cycloisomerization of acyclic dienyl esters to cyclohexyl β-lactones. Derivatizations avail cyclohexenes bearing four contiguous stereogenic centers, while mechanistic studies support olefin isomerization prior to cyclization.
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