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

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 aci...

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Bibliographic Details
Published in:Tetrahedron 2015-01, Vol.71 (2), p.245-251
Main Authors: Reid, Caroline M., Fanning, Kate N., Fowler, Lindsay S., Sutherland, Andrew
Format: Article
Language:English
Subjects:
2-Oxosilanes
4-Oxo-l-norvaline
Amino acids
Aspartic acid
Bonding
Chlorides
Cleavage
Derivatives
Homologation
Peterson olefination
Synthesis (chemistry)
Tetrahedrons
α-Amino acids
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.11.059