75857-93-1Relevant articles and documents
Hydroboration of vinylglycine and allylglycine as a route to boron- derivatives of α-amino acids
Denniel, Valerie,Bauchat, Patrick,Danion, Daniel,Danion-Bougot, Renee
, p. 5111 - 5114 (1996)
The hydroboration of protected vinylglycine and allylglycine with dicyclohexyl- or diisopinocampheylborane occurs chimio- and regioselectively with attachment of boron to the less substituted end of the carbon-carbon double bond. Homoserine or δ-hydroxynorvaline are readily obtained by H2O2/CH3CO2Na oxidation of dicyclohexylborane derivatives and 2-amino-4- boronobutanoic acid or 2-amino-5-boronopentanoic acid by reaction of diisopinocampheylborane derivatives with excess of ethanal and deprotection.
Oxidative functionalization of aliphatic and aromatic amino acid derivatives with H2O2 catalyzed by a nonheme imine based iron complex
Ticconi, Barbara,Colcerasa, Arianna,Di Stefano, Stefano,Lanzalunga, Osvaldo,Lapi, Andrea,Mazzonna, Marco,Olivo, Giorgio
, p. 19144 - 19151 (2018/05/31)
The oxidation of a series of N-acetyl amino acid methyl esters with H2O2 catalyzed by a very simple iminopyridine iron(ii) complex 1 easily obtainable in situ by self-assembly of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 was investigated. Oxidation of protected aliphatic amino acids occurs at the α-C-H bond exclusively (N-AcAlaOMe) or in competition with the side-chain functionalization (N-AcValOMe and N-AcLeuOMe). N-AcProOMe is smoothly and cleanly oxidized with high regioselectivity affording exclusively C-5 oxidation products. Remarkably, complex 1 is also able to catalyze the oxidation of the aromatic N-AcPheOMe. A marked preference for the aromatic ring hydroxylation over Cα-H and benzylic C-H oxidation was observed, leading to the clean formation of tyrosine and its phenolic isomers.
SYNTHESIS OF 2-OXA AND 2-AZA ANALOGS OF PYRROLIZIDINE-3,5-DIONES (LUKES-SORM DILACTAM)
Nagasaka, Tatsuo,Hakamada, Rie,Kunii, Shin-ichi,Hamaguchi, Fumiko
, p. 619 - 630 (2007/10/02)
The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported.Optically active (+)-2-oxa and (+)-2-aza analogs and racemic 2-aza analog and its 1-methoxycarbonyl derivatives were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.