A [3,3]-sigmatropic process catalysed by acetate. The decarboxylative Claisen rearrangement

被引：17

作者：

Bourgeois, D ^{[1
]}

Craig, D ^{[1
]}

Grellepois, F ^{[1
]}

Mountford, DM ^{[1
]}

Stewart, AJW ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

基金：

英国工程与自然科学研究理事会;

关键词：

acetate-catalysed; claisen rearrangement; decarboxylation; regiospecific allylation;

D O I：

10.1016/j.tet.2005.09.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylic tosylacetates and tosylmalonates undergo acetate-catalysed decarboxylative Claisen rearrangement in the presence of N,O-bis(trimethylsilyl)acetamide. The homoallylic sulfones formed in these transformations correspond to the products of regiospecific allylation of sulfone-stabilised carbanions. A mechanistic rationale is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：483 / 495

页数：13

共 38 条

[1] ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES [J].

AUBURN, PR ;

MACKENZIE, PB ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2033-2046

[2] Synthesis of homoallylic sulfones through a decarboxylative Claisen rearrangement reaction [J].

Bourgeois, D ;

Craig, D ;

King, NP ;

Mountford, DM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :618-621

[3]

BOURGEOIS D, 2005, ANGEW CHEM INT EDIT, V117, P524

[4] REMOTE SUBSTITUENT EFFECTS IN MICROBIAL REDUCTIONS OF 3-KETOGLUTARATE AND 3-KETOADIPATE ESTERS [J].

BROOKS, DW ;

DELEE, NC ;

PEEVEY, R .

TETRAHEDRON LETTERS, 1984, 25 (41) :4623-4626

[5] Ruthenium-catalyzed stereospecific decarboxylative allylation of non-stabilized ketone enolates [J].

Burger, EC ;

Tunge, JA .

CHEMICAL COMMUNICATIONS, 2005, (22) :2835-2837

[6] Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate [J].

Burger, EC ;

Tunge, JA .

ORGANIC LETTERS, 2004, 6 (22) :4113-4115

[7] Ruthenium-catalyzed decarboxylative allylation of nonstabilized ketone enolates [J].

Burger, EC ;

Tunge, JA .

ORGANIC LETTERS, 2004, 6 (15) :2603-2605

[8] Addition of alpha beta-unsaturated alcohols to the active methylene group Part I The action of ethyl acetoacetate on linalool and geraniol [J].

Carroll, MF .

JOURNAL OF THE CHEMICAL SOCIETY, 1940, :704-706

[9] Claisen rearrangement over the past nine decades [J].

Castro, AMM .

CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002

[10] New aspects of the Ireland and related Claisen rearrangements [J].

Chai, YH ;

Hong, SP ;

Lindsay, HA ;

McFarland, C ;

McIntosh, MC .

TETRAHEDRON, 2002, 58 (15) :2905-2928

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