Enantioselective alpha-silyl amino acid synthesis by reverse-aza-Brook rearrangement.
[reaction: see text] Asymmetric reverse-aza-Brook rearrangement of N-Boc-N-trialkylsilyl allylamine yields an enantiomerically enriched alpha-amino allylsilane. Oxidative cleavage of the alkene leads to a Boc-protected amino acid with the configuration of naturally occurring amino acids (L). Standard coupling protocols, including the use of trifluoroacetic acid for removal of the Boc group, yield a tripeptide with a central silane amino acid.
Liu
Guodong
G
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
Sieburth
Scott McN
SM
D000499:Allylamine / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry
D000596:Amino Acids; D010455:Peptides; D012821:Silanes; D000499:Allylamine; D014269:Trifluoroacetic Acid