- Enantioselective Synthesis of γ-Hydroxynorvaline
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A new synthesis of enantiomerically pure γ-hydroxynorvaline is described. The key step involves diastereoselective alkylation of the chiral Schiff base 1 with primary iodo derivatives 2 easily prepared from propylene oxide.
- Jacob,Roumestant,Viallefont,Martinez
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- Stereoselective Synthesis of syn -γ-Hydroxynorvaline and Related α-Amino Acids
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The total syntheses of three enantiomerically pure non-proteinogenic amino acids, l -norvaline, γ-oxonorvaline, and syn -γ-hydroxynorvaline, are reported. The chromatography-free route pivoted on the construction of highly enantiomerically enriched substituted α-amino-γ-oxopentanoic acid, from which all three members were accessed divergently via chemoselective and stereoselective reductions. The rapid synthesis of this key α-amino-γ-oxopentanoic acid was achieved by a highly diastereoselective crystallisation-driven three-component Mannich reaction from the readily available building blocks acetone, glyoxylic acid monohydrate, and (S)-(4-methoxyphenyl)ethylamine. The enantiomeric purity of all target molecules was confirmed by HPLC analysis, either of the amino acids or their derivatives.
- Berke?, Du?an,Caletková, O?ga,Ferko, Branislav,Jakubec, Pavol,Kolarovi?, Andrej,Puch?ová, Eva,Valachová, Dominika
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p. 4568 - 4575
(2019/12/11)
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- Asymmetric Induction in Acyclic Radical Reactions: Enantioselective Syntheses of α-Amino Acids via Carbon-Carbon Bond Forming Radical Reactions.
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The derivative of glycine, 8-phenylmenthyl N-Boc-2-bromoglycinate 1 reacted with allyltri-n-butylstannanes via the corresponding radical 2 by the SH2' mechanism to give (2S) allyl amino acid derivatives with high diastereoselectivity.The reaction of 1 with triphenyl(1,2-propadienyl)stannane and triphenyl(2-propynyl)stannane gave the (2S) allenyl and (2S) propargyl amino acid derivatives respectively also with high diastereoselectivity but by a different mechanism.
- Hamon, David P. G.,Massy-Westropp, Ralph A.,Razzino, Pasquale
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p. 4183 - 4194
(2007/10/02)
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- ENANTIOSELECTIVE SYNTHESIS OF HYDROXY α-AMINO ACIDS. (-)-erythro- and (-)-threo-γ-HYDROXYNORVALINES
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The amino acids (-)-erythro- and (-)-threo-γ-hydroxynorvaline have been synthesized from D-ribonolactone, 6, as single chiral precursor.Moreover, β-hydroxy-α-azido-γ-valerolactones 12a and 12b have been also prepared from 6 in two different alternative wa
- Ariza, Jesus,Font, Josep,Ortuno, Rosa M.
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p. 1931 - 1942
(2007/10/02)
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