- Enantioselective synthesis of 2-substituted 3-aminopropanoic acid (β-alanine) derivatives which are β-analogues of aromatic amino acids
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3-Aminopropanoic acid derivatives with a phenyl, 4-hydroxyphenyl, benzyl or indol-3-yl substituent at C-2 can be prepared enantioselectively by routes involving electrophilic attack of synthetic equivalents of [H2NCH2]+ upon enolates derived from chiral 3-acyl-1,3-oxazolidin-2-ones. tert-Butyl bromoacetate may be used as the electrophile, with subsequent introduction of nitrogen through the Curtius reaction, using the sequence of reagents (i) CF3CO2H; (ii) (PhO)2P(O)N3, Et3N, PhCH2OH; alternatively, direct electrophilic reaction with 1-[N-(benzyloxycarbonyl)aminomethyl]benzotriazole 4c or benzyl N-(acetoxymechyl)carbamate 2d introduces a protected aminomethyl group in a single step.
- Arvanitis, Elena,Ernst, Holger,Ludwig, Alice A.,Robinson, Andrew J.,Wyatt, Peter B.
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p. 521 - 528
(2007/10/03)
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- (R)-(+)-3-Amino-2-phenylpropanoic Acid: a Revised Absolute Configuration based on an Enantioselective Synthesis and an X-Ray Crystal Structure of the Salt with (1S)-(+)-Camphor-10-sulfonic Acid
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Amidoalkylation of the lithium enolate of (4S,5R)-4-methyl-5-phenyl-3-(phenylacetyl)oxazolidin-2-one 5 by 1-(N-benzyloxycarbonylaminomethyl)benzotriazole 2c, followed by cleavage of the oxazolidinone chiral auxiliary and of the N-benzyloxycarbonyl group, gave (R)-(+)-3-amino-2-phenylpropanoic acid 1, the absolute configuration of which was determined by X-ray crystallography on the salt 8 with (1S)-(+)-camphor-10-sulfonic acid.
- D'Souza, Alice A.,Motevalli, Majid,Robinson, Andrew J.,Wyatt, Peter B.
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