ArticleAngewandte Chemie (International ed. in English)2014
Stereocontrolled synthesis of syn-β-Hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Biocatalytic asymmetric aldol addition into unactivated ketones.Nature chemistry · 2024Article
- Asymmetric Hydrative Aldol Reaction (HAR) via Vinyl-Gold Promoted Intermolecular Ynamide Addition to Aldehydes.Angewandte Chemie (International ed. in English) · 2023Article
- Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores.Journal of the American Chemical Society · 2021Article
- Exploration of Iron- and a-Ketoglutarate-Dependent Dioxygenases as Practical Biocatalysts in Natural Product Synthesis.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
- Asymmetric assembly of high-value α-functionalized organic acids using a biocatalytic chiral-group-resetting process.Nature communications · 2018Article
- Large-scale preparation of key building blocks for the manufacture of fully synthetic macrolide antibiotics.The Journal of antibiotics · 2018Article
- Selective alkylation/oxidation ofTetrahedron letters · 2017Article
- An L-threonine transaldolase is required for L-threo-β-hydroxy-α-amino acid assembly during obafluorin biosynthesis.Nature communications · 2017Article
- Oxidative diversification of amino acids and peptides by small-molecule iron catalysis.Nature · 2016Article
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5 authors.
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Abstract
β-Hydroxy-α-amino acids figure prominently as chiral building blocks in chemical synthesis and serve as precursors to numerous important medicines. Reported herein is a method for the synthesis of β-hydroxy-α-amino acid derivatives by aldolization of pseudoephenamine glycinamide, which can be prepared from pseudoephenamine in a one-flask protocol. Enolization of (R,R)- or (S,S)-pseudoephenamine glycinamide with lithium hexamethyldisilazide in the presence of LiCl followed by addition of an aldehyde or ketone substrate affords aldol addition products that are stereochemically homologous with L- or D-threonine, respectively. These products, which are typically solids, can be obtained in stereoisomerically pure form in yields of 55-98 %, and are readily transformed into β-hydroxy-α-amino acids by mild hydrolysis or into 2-amino-1,3-diols by reduction with sodium borohydride. This new chemistry greatly facilitates the construction of novel antibiotics of several different classes.
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