Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0040-4039(99)01606-8
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. 
Zhou, J.-R.
Li, X.-R. 
Sim, K.-Y. 
Keywords: Aminocyclization
Chiral template
Diastereoselectivity
Reduction
Synthesis
Issue Date: 29-Oct-1999
Source: 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
URI: http://scholarbank.nus.edu.sg/handle/10635/75459
ISSN: 00404039
DOI: 10.1016/S0040-4039(99)01606-8
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

14
checked on Apr 24, 2018

WEB OF SCIENCETM
Citations

15
checked on Apr 24, 2018

Page view(s)

50
checked on Apr 20, 2018

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.