Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-β-Hydroxy Aspartic Acid

Merino, Pedro; Franco, Santiago; Merchán, F. L.; Tejero, Tomás

doi:10.3390/30100026

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Cited by 6 publications

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A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid

Khalaf

Datta

2007

Amino Acids

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3-Hydroxyaspartic acid and its derivatives are found both in the free form and as peptide constituents in various microorganisms and fungi. Considering the biological importance of this amino acid and its potential utility as a multifunctional building block in organic syntheses, we have developed a short-step, asymmetric synthetic route to a strategically protected 3-hydroxyaspartic acid derivative in enantiopure form. The key steps in the synthesis involve, Sharpless asymmetric aminohydroxylation of commercially available trans-ethyl cinnamate, and, utilization of the phenyl group as a masked carboxylic acid synthon towards construction of the complete structural framework of the title compound.

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A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid

Khalaf

Datta

2007

Amino Acids

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Chapter 2 Recent advances in the reaction of metalated aromatic heterocycles with carbonyl compounds and their imino derivatives

Merino¹

1999

A Critical Review of the 1998 Literature Preceded by Two Chapters on Current Heterocyclic Topics

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Studies on cyclization reactions of 3-amino-2,4-dihydroxybutanoic acid derivatives

et al. 2017

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A number of cyclic derivatives of 3-amino-2,4-dihydroxybutanoic acid are known in the literature but they are often prepared from other cyclic precursors. This study showed that the title compound too may serve as a convenient substrate for cyclization reactions. Using orthogonally-protected linear derivatives, regioselective cyclizations were performed, leading to original and highly-functionalized γ-lactones, oxazolidinones, oxazolines and aziridines. In these reactions a key role was played by the C3 nitrogen group function, while the C2 alcohol function showed no propensity for participation in cyclization reactions.

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Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-β-Hydroxy Aspartic Acid

Cited by 6 publications

References 37 publications

A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid

A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid

Chapter 2 Recent advances in the reaction of metalated aromatic heterocycles with carbonyl compounds and their imino derivatives

Studies on cyclization reactions of 3-amino-2,4-dihydroxybutanoic acid derivatives

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