Versatile solid-phase synthesis of peptide-derived 2-oxazolines. Application in the synthesis of ligands for asymmetric catalysis

被引：20

作者：

Benito, JM ^{[1
]}

Christensen, CA ^{[1
]}

Meldal, M ^{[1
]}

机构：

[1] SPOCC Ctr, Carlsberg Lab, DK-2500 Valby, Denmark

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 04期

关键词：

D O I：

10.1021/ol047675h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：581 / 584

页数：4

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