Asymmetric Intramolecular Carbolithiation of Achiral Substrates: Synthesis of Enantioenriched (R)-(+)-Cuparene and (R)-(+)-Herbertene
The Journal of Organic Chemistry2014Vol. 79(21), pp. 10722–10726
Citations Over TimeTop 25% of 2014 papers
Abstract
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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