Daly, M., Cant, A.A., Fowler, L.S., Simpson, G.L., Senn, H.M. and Sutherland, A. (2012) Switching the stereochemical outcome of 6-endo-trig cyclizations; Synthesis of 2,6-Cis-6-substituted 4-oxopipecolic acids. Journal of Organic Chemistry, 77(22), pp. 10001-10009. (doi: 10.1021/jo3022583)
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73070.pdf - Accepted Version 390kB |
Abstract
A base-mediated 6-endo-trig cyclization of readily accessible enone-derived α-amino acids has been developed for the direct synthesis of novel 2,6-cis-6- substituted-4-oxo-L-pipecolic acids. A range of aliphatic and aryl side chains were tolerated by this mild procedure to give the target compounds in good overall yields. Molecular modeling of the 6-endo-trig cyclization allowed some insight as to how these compounds were formed, with the enolate intermediate generated via an equilibrium process, followed by irreversible tautomerization/neutralization providing the driving force for product formation. Stereoselective reduction and deprotection of the resulting 2,6-cis-6-substituted 4-oxo-L-pipecolic acids to the corresponding 4-hydroxy-L-pipecolic acids was also performed.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Fowler, Miss Lindsay and Senn, Dr Hans and Cant, Mr Alastair and Sutherland, Professor Andrew and Daly, Mr Mark |
| Authors: | Daly, M., Cant, A.A., Fowler, L.S., Simpson, G.L., Senn, H.M., and Sutherland, A. |
| Subjects: | Q Science > QD Chemistry |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Journal Abbr.: | J. Org. Chem. |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Published Online: | 05 November 2012 |
| Copyright Holders: | Copyright © 2012 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 77(22):10001-10009 |
| Publisher Policy: | Reproduced in accordance with the copyright policy of the publisher |
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