Preparation of enantiomerically pure protected 4-oxo .alpha.-amino acids and 3-aryl .alpha.-amino acids from serine

Jackson, Richard F. W.; Wishart, Neil; Wood, Anthony; James, K.; Wythes, Martin

doi:10.1021/jo00038a030

Cited by 196 publications

(60 citation statements)

References 1 publication

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“…Early work by Knochel and co-workers demonstrated that alkyl zinc reagents prepared by the reaction of zinc dust with an appropriate organohalide were not destroyed in the presence of acidic protons (pK a [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. [157,158] In 2006, Uchiyama et al reported that the halogen-metal exchange of a haloarenes bearing acidic hydrogen atoms could be accomplished with tBu 4 ZnLi 2 without quenching the reagent or the resulting aryl zincate. [159] For example, treatment of p-iodobenzylalcohol (192) with tBu 4 ZnLi 2 generated 193, which could be trapped with a variety of electrophiles in moderate to high yields (Scheme 80).…”

Section: Selecting Between Carbon-carbon Coupling Reactionsmentioning

confidence: 99%

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

2009

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Achieving high levels of chemoselectivity has been the Achilles' heel of chemical synthesis. The excitement generated by the successful realization of chemoselective strategies underscores the painstaking efforts to define a set of conditions conducive to selection among the available reaction pathways. We discuss in this Review various aspects of chemoselectivity that have been addressed in a range of synthetic methods over the past decade. We have focused on the proposed mechanistic basis of the reactions under consideration in an attempt to categorize them and highlight the key concepts that have been emerging on the basis of these studies. Our overview of recent advances in chemoselective processes suggests that significant progress has been made, but a lot of challenges lie ahead.

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Section: Selecting Between Carbon-carbon Coupling Reactionsmentioning

confidence: 99%

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

2009

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“…In contrast to these aromatic amino acids bearing (pseudo)halogenated moieties, amino acid-based alkyl halides are not used directly as substrates in the Suzuki-Miyaura reaction. To date, their use is limited to the Negishi reaction of β-iodoalanine, β-iodohomoalanine, and iodobishomoalanine with various aryl iodides, to gain access to non-proteinogenic phenylalanine analogues [66][67][68][69]. For peptides that are prepared by chemical methods, SPPS easily enables the replacement of an aromatic amino acid with a non-natural (pseudo)halogenated analogue.…”

Section: Access To and Derivatization Of (Pseudo)halogenated Aromaticmentioning

confidence: 99%

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

et al. 2017

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Abstract:The (site-selective) derivatization of amino acids and peptides represents an attractive field with potential applications in the establishment of structure-activity relationships and labeling of bioactive compounds. In this respect, bioorthogonal cross-coupling reactions provide valuable means for ready access to peptide analogues with diversified structure and function. Due to the complex and chiral nature of peptides, mild reaction conditions are preferred; hence, a suitable cross-coupling reaction is required for the chemical modification of these challenging substrates. The Suzuki reaction, involving organoboron species, is appropriate given the stability and environmentally benign nature of these reactants and their amenability to be applied in (partial) aqueous reaction conditions, an expected requirement upon the derivatization of peptides. Concerning the halogenated reaction partner, residues bearing halogen moieties can either be introduced directly as halogenated amino acids during solid-phase peptide synthesis (SPPS) or genetically encoded into larger proteins. A reversed approach building in boron in the peptidic backbone is also possible. Furthermore, based on this complementarity, cyclic peptides can be prepared by halogenation, and borylation of two amino acid side chains present within the same peptidic substrate. Here, the Suzuki-Miyaura reaction is a tool to induce the desired cyclization. In this review, we discuss diverse amino acid and peptide-based applications explored by means of this extremely versatile cross-coupling reaction. With the advent of peptide-based drugs, versatile bioorthogonal conversions on these substrates have become highly valuable.

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“…This compound, which is easily derived from l-serine in a four-step sequence, [26] was treated with the enamine 12 derived from cyclohexanone and pyrrolidine to give 14. Removal of the N-Boc protecting group provided an amino ester, which cyclized to 15 upon heating under acidic conditions.…”

Section: Dubuffet and Langlois Reportedmentioning

confidence: 99%

Access to the cis‐Fused Stereoisomers of Proline Analogues Containing an Octahydroindole Core

et al. 2011

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An overview of the synthetic methods developed to build all the cis‐fused stereoisomers of octahydroindole‐2‐carboxylic acid and its α‐methylated derivative in enantiomerically pure form is presented. Both asymmetric synthetic strategies(auxiliary‐ or substrate‐controlled processes) and procedures based on the resolution of racemic compounds (chemical, enzymatic, and chromatographic processes) are summarized. Special emphasis has been placed on those strategies able to provide multigram quantities of enantiopure compounds, a prerequisite to make downstream biological applications feasible.

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Preparation of enantiomerically pure protected 4-oxo .alpha.-amino acids and 3-aryl .alpha.-amino acids from serine

Cited by 196 publications

References 1 publication

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

Access to the cis‐Fused Stereoisomers of Proline Analogues Containing an Octahydroindole Core

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