Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines
by Gawley, R. E.; Barolli, G.; Madan, S.; Saverin, M.; 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.
- Journal
- Tetrahedron Letters
- Volume
- 45
- Issue
- 8
- Year
- 2004
- Start Page
- 1759-1761
- URL
- https://dx.doi.org/10.1016/j.tetlet.2003.12.080
- ISBN/ISSN
- 1873-3581; 0040-4039
- DOI
- 10.1016/j.tetlet.2003.12.080