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|Title:||A novel reductive aminocyclization for the syntheses of chiral pyrrolidines: Stereoselective syntheses of (S)-nornicotine and 2-(2'-pyrrolidyl)-pyridines|
|Authors:||Loh, T.-P. |
|Citation:||Loh, 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|
|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.|
|Source Title:||Tetrahedron Letters|
|Appears in Collections:||Staff Publications|
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