Allylations of chelated enolates using dienyl substrates

被引：9

作者：

Basak, Sankar ^{[1
]}

Kazmaier, Uli ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 03期

关键词：

D O I：

10.1021/ol702865q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isomerization-free reactions of dienyl carbonates (1-3) with chelated amino acid ester enolates at -78 degrees C provide important information concerning the mechanism of these dienylations. The formation of regioisomeric products can be explained by competing S(N)2/S(N)2' reactions, and the product distribution can be influenced by proper choice of the reaction conditions.

引用

页码：501 / 504

页数：4

共 69 条

[31]

Kazmaier U., 2004, METAL CATALYZED CROS, P531

[32]

Kazmaier U., 2005, ANGEW CHEM, V117, P3368

[33]

Kazmaier U., 2006, ANGEW CHEM, V118, P3143

[34] Influences on the regioselectivity of palladium-catalyzed allylic alkylations [J].

Kazmaier, Uli ;

Stolz, Daniel ;

Kraemer, Katia ;

Zumpe, Franz L. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (04) :1322-1329

[35] Highly stereoselective allylic alkylations of peptides [J].

Kazmaier, Uli ;

Deska, Jan ;

Watzke, Anja .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (29) :4855-4858

[36] Regio- and stereoselective rhodium-catalyzed allylic alkylations of chelated enolates [J].

Kazmaier, Uli ;

Stolz, Daniel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3072-3075

[37] Isomerization-free allylic alkylations of terminal π-allyl palladium complexes [J].

Kraemer, Katja ;

Kazmaier, Uli .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8950-8953

[38] Substrate-controlled palladium-catalyzed allylic alkylations of chelated enolates - Scope and limitations [J].

Lindner, T ;

Kazmaier, U .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1687-1695

[39] Regio- and enantioselective iridium-catalyzed allylic alkylation with in situ activated P,C-chelate complexes [J].

Lipowsky, G ;

Miller, N ;

Helmchen, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (35) :4595-4597

[40] Regio- and enantioselective iridium-catalysed allylic aminations and alkylations of dienyl esters [J].

Lipowsky, G ;

Helmchen, G .

CHEMICAL COMMUNICATIONS, 2004, (01) :116-117

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