β-Olefination of 2-Alkynoates Leading to Trisubstituted 1,3-Dienes

被引：27

作者：

Jacobsen, Mathias J.

Funder, Erik Daa

Cramer, Jacob R.

Gothelf, Kurt V. ^{[1
]}

机构：

[1] Danish Natl Res Fdn, Ctr DNA Nanotechnol CDNA, Langelandsgade 140, DK-8000 Aarhus C, Denmark

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 13期

基金：

新加坡国家研究基金会;

关键词：

PHOSPHINE-MEDIATED OLEFINATION; ELECTRON-WITHDRAWING GROUPS; CATALYZED 3+2 CYCLOADDITION; BIFUNCTIONAL ACETYLENES; ALPHA-ADDITION; STEREOSELECTIVE-SYNTHESIS; WITTIG OLEFINATION; TRIPHENYLPHOSPHINE; POLYADDITION; ALLENOATES;

D O I：

10.1021/ol2011677

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphine-mediated olefination of 2-alkynoates with aldehydes forming 1,3-dienes with high E-selectivity and up to 88% yield is described. Reaction conditions are optimized and reactions are demonstrated for,various aryl, alkyl, and alkenyl aldehydes and for ethyl 2-alkynoates with different substituents in the delta-position. Proof of concept is shown for the generation of a beta,gamma-unsaturated lactone by intramolecular olefination, and furthermore the use of the generated 1,3-dienes in the Diels-Alder reaction has been demonstrated.

引用

收藏

页码：3418 / 3421

页数：4

相关论文

共 57 条

[1] Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction [J].

Alvarez-Ibarra, C ;

Csáky, AG ;

de la Oliva, CG .

TETRAHEDRON LETTERS, 1999, 40 (48) :8465-8467

[2] Synthesis of γ,δ-didehydrohomoglutamates by the phosphine-catalyzed γ-addition reaction to acetylenic esters [J].

Alvarez-Ibarra, C ;

Csáky, AG ;

de la Oliva, CG .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3544-3547

[3] A Novel Approach to the Synthesis of Highly Functionalized Pyrroles [J].

Anary-Abbasinejad, Mohammad ;

Charkhati, Khadije ;

Anaraki-Ardakani, Hossein .

SYNLETT, 2009, (07) :1115-1117

[4] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].

Blakemore, PR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585

[5] Phosphine-Catalyzed Enantioselective Synthesis of Oxygen Heterocycles [J].

Chung, Ying Kit ;

Fu, Gregory C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2225-2227

[6] Functionalized 1-alkoxy-1,3-dienes: Their preparation and applications in synthetic organic [J].

Deagostino, Annamaria ;

Prandi, Cristina ;

Zavattaro, Chiara ;

Venturello, Paolo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (11) :2463-2483

[7] Isolation and phytotoxicity of apocarotenoids from Chenopodium album [J].

DellaGreca, M ;

Di Marino, C ;

Zarrelli, A ;

D'Abrosca, B .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (09) :1492-1495

[8] Enyne metathesis (enyne bond reorganization) [J].

Diver, ST ;

Giessert, AJ .

CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382

[9] Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations [J].

Doucet, Henri ;

Hierso, Jean-Cyrille .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :834-871

[10] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

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