Keith James
Scripps Research Institute
17 Papers
329 Citations
Keith James is an academic researcher from Scripps Research Institute. The author has contributed to research in topics: Aryl & Chemistry. The author has an hindex of 14, co-authored 17 publications.
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Papers
Preparation of enantiomerically pure protected 4-oxo .alpha.-amino acids and 3-aryl .alpha.-amino acids from serine
TL;DR: The organozinc reagent 13, prepared from the protected β-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-α-amino acids 17 in 39-90% yield.
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Synthesis of 5-iodo-1,2,3-triazole-containing macrocycles using copper flow reactor technology.
Andrew Bogdan,Keith James +1 more
TL;DR: A new macrocyclization strategy to synthesize 12- to 31-membered 5-iodo-1,2,3-triazole-containing macrocycles is described, and this methodology also permits the facile, regioselective synthesis of 1,4,5-trisubstituted-1-2, 3-trizole- containing macrocyles using palladium-catalyzed cross-coupling reactions.
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Efficient access to new chemical space through flow--construction of druglike macrocycles through copper-surface-catalyzed azide-alkyne cycloaddition reactions.
Andrew Bogdan,Keith James +1 more
TL;DR: A series of 12- to 22-membered macrocycles, with druglike functionality and properties, have been generated by using a simple and efficient copper-catalyzed azide-acetylene cycloaddition reaction, conducted in flow in high-temperature copper tubing, under environmentally friendly conditions.
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Strained cyclophane macrocycles: impact of progressive ring size reduction on synthesis and structure.
TL;DR: The most strained system prepared represents the first report of an 11-membered cyclophane containing a 1,4-disubstituted 1,2,3-triazole ring and establishes a limit to the ring strain that can be generated using this macrocycle synthesis methodology.
83
Emac – a comparative index for the assessment of macrocyclization efficiency
James C. Collins,Keith James +1 more
TL;DR: A macrocyclization efficiency index, Emac, is proposed, which takes into account both reaction yield and concentration and is presented, along with selected examples of high and low efficiency macrocyclizations.
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