Synthesis and reactivity of 4-oxo-5-trimethylsilanyl derived α-amino acids

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:Sutherland, Professor Andrew and Fanning, Ms Kate and Reid, Miss Caroline and Fowler, Miss Lindsay
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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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
466652EPSRC Doctoral Training Account (DTA) 2007-2011Mary GoodmanEngineering & Physical Sciences Research Council (EPSRC)EP/P503582/1VICE PRINCIPAL RESEARCH & ENTERPRISE