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Asymmetric Intramolecular Carbolithiation of Achiral Substrates: Synthesis of Enantioenriched (R)‑(+)-Cuparene and (R)‑(+)-Herbertene

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posted on 2014-11-07, 00:00 authored by Matthew R. Luderer, Michael J. Mealy, William F. Bailey
Concise syntheses of the sesquiterpenes (R)-(+)-cuparene and (R)-(+)-herbertene by asymmetric cyclization of achiral olefinic alkyllithium precursors in the presence of (−)-sparteine are reported. The quaternary stereogenic center in each product is set at the final step of the synthesis by enantioselective (er = 61:39) 5-exo ring closure.

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