Highly stereoselective modifications of peptides via Pd-catalyzed allylic alkylation of internal peptide amide enolates

被引：28

作者：

Datta, Swarup ^{[1
]}

Bayer, Anton ^{[1
]}

Kazmaier, Uli ^{[1
]}

机构：

[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 41期

关键词：

AMINO-ACID; CLAISEN REARRANGEMENT; SAMARIUM DIIODIDE; C-ALKYLATIONS; SIDE-CHAINS; PALLADIUM; RESIDUES; LITHIUM; DERIVATIVES; CHEMISTRY;

D O I：

10.1039/c2ob26351c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd-catalyzed allylations are excellent tools for stereoselective peptide modifications, showing several advantages compared to normal alkylations. Reactions of internal peptide amide enolates with Pd-allyl complexes proceed not only with high yields of up to 86%, they show also high regio- and diastereoselectivities (88-99%), giving rise to the trans-configured products. Therefore, this protocol is a powerful synthetic tool for the synthesis of natural product and drug molecules.

引用

页码：8268 / 8275

页数：8

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