Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0040-4039(99)01606-8
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dc.titleA novel reductive aminocyclization for the syntheses of chiral pyrrolidines: Stereoselective syntheses of (S)-nornicotine and 2-(2'-pyrrolidyl)-pyridines
dc.contributor.authorLoh, T.-P.
dc.contributor.authorZhou, J.-R.
dc.contributor.authorLi, X.-R.
dc.contributor.authorSim, K.-Y.
dc.date.accessioned2014-06-23T05:30:37Z
dc.date.available2014-06-23T05:30:37Z
dc.date.issued1999-10-29
dc.identifier.citationLoh, T.-P., Zhou, J.-R., Li, X.-R., Sim, K.-Y. (1999-10-29). A novel reductive aminocyclization for the syntheses of chiral pyrrolidines: Stereoselective syntheses of (S)-nornicotine and 2-(2'-pyrrolidyl)-pyridines. Tetrahedron Letters 40 (44) : 7847-7850. ScholarBank@NUS Repository. https://doi.org/10.1016/S0040-4039(99)01606-8
dc.identifier.issn00404039
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/75459
dc.description.abstract(S)-Nornicotine 2 was synthesized in four steps. A key step in the synthesis involved reductive aminocyclization of a 1,4-ketoaldehyde with 2,3,4,6-tetra-O-pivaloyl-β-D-galactosylamine 1 in the presence of sodium cyanoborohydride, diastereoselectively affording the corresponding stereoisomer 6 in 45% yield. The aminosugar moiety could be easily removed by acidic hydrolysis to furnish 2. The aminocyclization was further extended to asymmetric syntheses of novel chiral 2-(2'-pyrrolidyl)-pyridine ligands 12 and 13.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/S0040-4039(99)01606-8
dc.sourceScopus
dc.subjectAminocyclization
dc.subjectChiral template
dc.subjectDiastereoselectivity
dc.subjectReduction
dc.subjectSynthesis
dc.typeArticle
dc.contributor.departmentCHEMISTRY
dc.description.doi10.1016/S0040-4039(99)01606-8
dc.description.sourcetitleTetrahedron Letters
dc.description.volume40
dc.description.issue44
dc.description.page7847-7850
dc.description.codenTELEA
dc.identifier.isiut000083043400033
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