Diester-Substituted Aminocyclopropanes: Synthesis and Use in [3+2]-Annulation Reactions

被引：24

作者：

Serrano, Eloisa ^{[1
]}

de Nanteuil, Florian ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, EPFL SB ISIC LCSO, CH-1015 Lausanne, Switzerland

来源：

SYNLETT | 2014年 / 25卷 / 16期

基金：

瑞士国家科学基金会;

关键词：

annulation; carbocycles; homogenous catalysis; nitrogen; ring opening; DONOR-ACCEPTOR CYCLOPROPANES; 3+2 ANNULATION; CYCLOADDITION; CYCLOPROPYLAMINES; DERIVATIVES; CYCLIZATION; REARRANGEMENT; IMIDES;

D O I：

10.1055/s-0034-1378512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this Letter, we describe the synthesis of new donor-acceptor substituted cyclopropanes bearing various imido groups and their use in [3+2]-annulation reactions. A sequence of palladium-catalyzed vinylation and rhodium-catalyzed cyclopropanation gave access to the required cyclopropanes in only two steps and high overall yields. The obtained compounds were used successfully in the tin-catalyzed [3+2] annulation with enol ethers to give cyclopentylamine derivatives in 22-95% yield.

引用

页码：2285 / 2288

页数：4

共 36 条

[1] Baret N, 2000, EUR J ORG CHEM, V2000, P1507
[2] HOMOGENEOUS CATALYTIC VINYLATION OF CYCLIC IMIDES AND LACTAMS FOR THE SYNTHESIS OF N-VINYL MONOMERS
BAYER, E
GECKELER, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (07): : 533 - 534
[3] Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones
Benfatti, Fides
de Nanteuil, Florian
Waser, Jerome
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) : 4844 - 4849
[4] Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans
Benfatti, Fides
de Nanteuil, Florian
Waser, Jerome
[J]. ORGANIC LETTERS, 2012, 14 (01) : 386 - 389
[5] Heterocycles from cyclopropanes: applications in natural product synthesis
Carson, Cheryl A.
Kerr, Michael A.
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 3051 - 3060
[6] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations
Cavitt, Marchello A.
Phun, Lien H.
France, Stefan
[J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) : 804 - 818
[7] Dynamic Kinetic Asymmetric [3+2] Annulation Reactions of Aminocyclopropanes
de Nanteuil, Florian
Serrano, Eloisa
Perrotta, Daniele
Waser, Jerome
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (17) : 6239 - 6242
[8] Catalytic Friedel-Crafts Reaction of Aminocyclopropanes
de Nanteuil, Florian
Loup, Joachim
Waser, Jerome
[J]. ORGANIC LETTERS, 2013, 15 (14) : 3738 - 3741
[9] Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines
de Nanteuil, Florian
Waser, Jerome
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 12075 - 12079
[10] Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes
De Simone, Filippo
Saget, Tanguy
Benfatti, Fides
Almeida, Sofia
Waser, Jerome
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (51) : 14527 - 14538

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