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

被引：29

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

共 51 条

[1]

[Anonymous], ANGEW CHEM

[2] CONVERSION OF SERINE AND THREONINE RESIDUES INTO ALPHA-ACYLOXY-HALOGENOGLYCINE, ALPHA-ALKYLTHIO-HALOGENOGLYCINE, AND ALPHA-HALOGENOGLYCINE MOIETIES - A NEW STRATEGY FOR THE MODIFICATION OF PEPTIDES [J].

APITZ, G ;

STEGLICH, W .

TETRAHEDRON LETTERS, 1991, 32 (27) :3163-3166

[3] STUDY ON THE REGIOSELECTIVITY OF CARBANION SUBSTITUTION BY MEANS OF ALLYLIC DERIVATIVES CATALYZED TO PALLADIUM - SELECTIVE ACQUISITION OF COMPOUNDS WITH QUARTERNARY CARBON-ATOMS [J].

CUVIGNY, T ;

JULIA, M ;

ROLANDO, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :395-413

[4] Stereoselective palladium-catalyzed allylic alkylations of peptide amide enolates [J].

Datta, Swarup ;

Kazmaier, Uli .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) :872-880

[5]

Deska J, 2007, ANGEW CHEM, V119, p[4570, 4654]

[6]

Deska J, 2008, CURR ORG CHEM, V12, P355

[7] Highly stereoselective peptide modifications through Pd-catalyzed allylic alkylations of chelated peptide enolates [J].

Deska, Jan ;

Kazmaier, Uli .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (21) :6204-6211

[8] Stereoselective syntheses and reactions of stannylated peptides [J].

Deska, Jan ;

Kazmaier, Uli .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4570-4573

[9] SELECTIVE MODIFICATION OF GLYCINE RESIDUES IN DIPEPTIDES [J].

EASTON, CJ ;

SCHARFBILLIG, IM ;

TAN, EW .

TETRAHEDRON LETTERS, 1988, 29 (13) :1565-1568

[10] Free-radical reactions in the synthesis of alpha-amino acids and derivatives [J].

Easton, CJ .

CHEMICAL REVIEWS, 1997, 97 (01) :53-82

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