T. Loh, J. Zhou, Xu-ran Li
Oct 29, 1999
Citations
1
Influential Citations
12
Citations
Journal
Tetrahedron Letters
Abstract
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 .