Journal ArticleDOI
Efficient Synthesis of Enantiopure β-Amino-γ-Keto Acids from l-Homoserine
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TLDR
In this paper, a variety of β-amino-γ-keto acids were prepared in four steps from commercially available l-homoserine, highlighted by a Ni-catalyzed Grignard addition to a N-protected derivative of l-Homoserine.About:
This article is published in Organic Letters.The article was published on 2003-05-17. It has received 12 citations till now. The article focuses on the topics: Derivative (chemistry) & Trimer.read more
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A copper-catalyzed, pH-neutral construction of high-enantiopurity peptidyl ketones from peptidic s-acylthiosalicylamides in air at room temperature.
TL;DR: A copper-catalyzed transformation of peptidic thiol esters and boronic acids gives peptidyl ketones and takes place in DMF or DMF/H(2)O at room temperature in air.
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Synthesis of High Enantiopurity N-Protected α-Amino Ketones by Thiol Ester-Organostannane Cross-Coupling using pH-Neutral Conditions
TL;DR: This Cu(I) diphenylphosphinate-mediated, palladium-catalyzed coupling of alpha-amino thiol esters with aryl, heteroaryl, allyl, and alkenyl organostannanes gives N-protected alpha- amino ketones in high yields with high enantiopurity under mild and pH-neutral reaction conditions.
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Trifluoroacetic anhydride-mediated solid-phase version of the Robinson-Gabriel synthesis of oxazoles.
TL;DR: A traceless solid-phase synthesis of oxazoles 4 via Robinson-Gabriel reaction of solid-supported alpha-acylamino ketones 2 has been achieved and a novel variant of the Ugi four-component reaction that allows for the preparation of compounds 2 in a single synthetic step is disclosed.
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CuI/RhII-Catalyzed Tandem Convergent Multicomponent Reaction for the Regio- and Stereocontrolled Synthesis of γ-Oxo-β-amino Esters
TL;DR: Rapid deconjugative [3,3]-sigmatropic rearrangement affords the α-vinyl γ-oxo-β-amino esters in high yields with high levels of diastereoselectivity.
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New Synthetic Strategy for High-Enantiopurity N-Protected α-Amino Ketones and their Derivatives by Asymmetric Hydrogenation
TL;DR: Asymmetric hydrogenation of α-dehydroamino ketones catalyzed by a rhodium-chiral phosphorus ligand complex (up to 99% ee, 1000 TON), represents an efficient approach to chiral α-amino kones as discussed by the authors.
References
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Journal ArticleDOI
beta-Peptides: from structure to function.
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Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis
TL;DR: The versatility of this technology was demonstrated by an example of selective drug delivery, where cells were decorated with biotin through selective conjugation to ketone groups, and selectively killed in the presence of a ricin A chain-avidin conjugate.
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Non-haemolytic β-amino-acid oligomers
TL;DR: In this article, a β-amino acid oligomer (β-peptide) was developed to mimic natural antibiotics and tested it for antimicrobial activity against four bacterial species including two pathogens that are resistant to common antibiotics.
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Recent advances in the stereoselective synthesis of β-amino acids
Mei Liu,Mukund P. Sibi +1 more
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Residue-based control of helix shape in beta-peptide oligomers.
Daniel H. Appella,Laurie A. Christianson,Daniel A. Klein,Douglas R. Powell,Xiaolin Huang,Joseph J. Barchi,Samuel H. Gellman +6 more
TL;DR: It is reported that β-amino acids can be used to design β-peptides with a very different secondary structure, a 12-helix, which demonstrates that by altering the nature of β- peptide residues, one can exert rational control over the secondary structure.