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Journal articles
Electrochemical access to 8-(1-phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the asymmetric syntheses of (+)-myrtine and alkaloid (+)-241D.
Abstract : The total syntheses of both enantiomers of trans-quinolizidine (+)-myrtine and cis-2,4,6-trisubstituted piperidine alkaloid (+)-241D are reported here. Our approach was based on the N-Boc-directed metalation of enantiopure 4-piperidone (-)-11, which was prepared in four steps from α-amino nitrile 6 through a stereoselective alkylation-reduction decyanation process. α-Amino nitrile 6 was prepared at the anode through electrochemical oxidation of 4-piperidone (+)-5. In our study, α-phenylethylamine (α-PEA) allowed an efficient 1-3 stereoinduction, and an orthogonal cleavage of the N-Boc protecting group in piperidone derivatives was carried out by stirring them in a suspension of SnCl4·(Et2O)2 complex in diethyl ether. When appropriate, the er's were determined by proton and carbon NMR spectroscopy utilizing (+)-tert-butylphenylphosphinothioic acid and (+)-DBTA as chiral solvating agents.
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01116313
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Friday, February 13, 2015 - 9:41:41 AM
Last modification on : Friday, November 26, 2021 - 2:46:29 PM
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Friday, February 13, 2015 - 9:41:41 AM
Last modification on : Friday, November 26, 2021 - 2:46:29 PM