Asymmetric intramolecular carbolithiation of achiral substrates: synthesis of enantioenriched (R)-(+)-cuparene and (R)-(+)-herbertene.

Autor: Luderer MR; Department of Natural Science, Mathematics, and Engineering, University of Pittsburgh at Greensburg , Greensburg, Pennsylvania 15601, United States., Mealy MJ, Bailey WF
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2014 Nov 07; Vol. 79 (21), pp. 10722-6. Date of Electronic Publication: 2014 Oct 23.
DOI: 10.1021/jo502139m
Abstrakt: 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.
Databáze: MEDLINE