Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines
by Gawley, Robert E.; Barolli, Graciela; Madan, Sachin; Saverin, Michele; O'Connor, S.
trans-Cumylcyclohexanol (TCC) is used as a chiral auxiliary for the stereoselective addition of tributyltinlithium to N-acylpyrrolidinium/piperidinium ion with 70-80% diastereoselectivity at 0degreesC. After removal of the minor diastereomer by radial chromatography, enantiopure N-methyl-2-(tributylstannyl)pyrrolidine and piperidine were produced by reductive removal of the auxiliary. (C) 2003 Elsevier Ltd. All rights reserved.
- Journal
- Tetrahedron Letters
- Volume
- 45
- Issue
- 8
- Year
- 2004
- Start Page
- 1759
- ISBN/ISSN
- 1873-3581; 0040-4039
- DOI
- 10.1016/j.tetlet.2003.12.080