Versatile solid-phase synthesis of peptide-derived 2-oxazolines. Application in the synthesis of ligands for asymmetric catalysis
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Versatile solid-phase synthesis of peptide-derived 2-oxazolines. Application in the synthesis of ligands for asymmetric catalysis. / Benito, Juan M.; Christensen, Christian A.; Meldal, Morten.
I: Organic Letters, Bind 7, Nr. 4, 17.02.2005, s. 581-584.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Versatile solid-phase synthesis of peptide-derived 2-oxazolines. Application in the synthesis of ligands for asymmetric catalysis
AU - Benito, Juan M.
AU - Christensen, Christian A.
AU - Meldal, Morten
PY - 2005/2/17
Y1 - 2005/2/17
N2 - (Chemical Equation Presented) A mild and high-yielding procedure for the solid-phase synthesis of 2-oxazolines from amino acids is described. The two-step protocol is based on the iodination of serine containing peptides, followed by in situ nucleophilic attack of the carbonyl oxygen from the next amino acid. Phosphinylation of the terminal amino group cleanly furnishes a resin-bound phosphine-oxazoline ligand, which upon palladium complexation was applied as catalyst in asymmetric allylic substitution.
AB - (Chemical Equation Presented) A mild and high-yielding procedure for the solid-phase synthesis of 2-oxazolines from amino acids is described. The two-step protocol is based on the iodination of serine containing peptides, followed by in situ nucleophilic attack of the carbonyl oxygen from the next amino acid. Phosphinylation of the terminal amino group cleanly furnishes a resin-bound phosphine-oxazoline ligand, which upon palladium complexation was applied as catalyst in asymmetric allylic substitution.
UR - http://www.scopus.com/inward/record.url?scp=14844357298&partnerID=8YFLogxK
U2 - 10.1021/ol047675h
DO - 10.1021/ol047675h
M3 - Journal article
C2 - 15704899
AN - SCOPUS:14844357298
VL - 7
SP - 581
EP - 584
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 4
ER -
ID: 326847627