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  • Title: A Nazarov-Ene Tandem Reaction for the Stereoselective Construction of Spiro Compounds.
    Author: Etling C, Tedesco G, Kalesse M.
    Journal: Chemistry; 2021 Jun 25; 27(36):9257-9262. PubMed ID: 33899295.
    Abstract:
    The different reactivity of trienones under Lewis and Brønsted acids catalysis was investigated, resulting in distinct cyclization products and carbon backbones that originated either from a conjugate Prins cyclization or an interrupted Nazarov cyclization. In particular, an unprecedented Nazarov cyclization tandem reaction is presented, terminating the oxyallyl cation by an ene-type reaction, and leading stereoselectively to bicyclic spiro compounds. The terminal olefin of this motif represents a useful handle for further functionalization, making it a strategic intermediate in total syntheses. The tandem Nazarov/ene cyclization was shown to be preferred over a Nazarov/[3+2] tandem reaction for all our substrates, independent of chain length. Deuteration studies further support the mechanistic hypothesis of the terminating ene reaction.
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