Reid, C. M., Fanning, K. N., Fowler, L. S. and Sutherland, A. (2015) Synthesis and reactivity of 4-oxo-5-trimethylsilanyl derived α-amino acids. Tetrahedron, 71(2), pp. 245-251. (doi: 10.1016/j.tet.2014.11.059)
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Abstract
A Lewis-acid promoted one-carbon homologation of an aspartic acid semialdehyde with trimethylsilyldiazomethane has led to the efficient synthesis of two silicon-containing α-amino acids. The use of trimethylaluminium or catalytic tin(II) chloride gave novel 4-oxo-5-trimethylsilanyl derived amino acids in yields of 71–88%. An investigation into the reactivity of these highly functional α-amino acids showed that selective cleavage of the C–Si bond could be achieved under mild basic conditions to give a protected derivative of the naturally occurring amino acid, 4-oxo-l-norvaline. Alternatively, Peterson olefination with aryl or alkyl aldehydes resulted in the formation of E-enone derived α-amino acids.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Reid, Miss Caroline and Fowler, Miss Lindsay and Sutherland, Professor Andrew and Fanning, Ms Kate |
| Authors: | Reid, C. M., Fanning, K. N., Fowler, L. S., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Tetrahedron |
| Publisher: | Elsevier |
| ISSN: | 0040-4020 |
| ISSN (Online): | 1464-5416 |
| Copyright Holders: | Copyright © 2014 The Authors |
| First Published: | First published in Tetrahedron 71(2):245-251 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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