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Short Paper | Special issue | Vol 86, No. 1, 2012, pp.727-734
Published online, 17th July, 2012
DOI: 10.3987/COM-12-S(N)27
Enantioselective Synthesis of cis- and trans-2-Methyl-6-nonylpiperidines: Alkaloids Solenopsin and Isosolenopsin

Mohamed Medjahdi, José Carlos González-Gómez,* Francisco Foubelo, and Miguel Yus*

*Department of Organic Chemistry, Faculty of Sciences and Institute of Organic Synthesis (ISO), University of Alicante, P.O. Box 99, 03080 Alicante, Spain

Abstract

The cross-metathesis of the enantioenriched homoallylic amine 8 (readily accessible by α-aminoallylation of decanal) with methyl vinyl ketone using the Hoveyda-Blechert catalyst 10 in presence of 10 mol% of Ti(O-i-Pr)4 led exclusively to the (E)-enone 11, which by stereoselective reductive amination affords (+)-isosolenopsin (3a) and (+)-solenopsin (4a) with excellent selectivities.