Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.

Literature DB >> 21486078

Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.

Matthew Hassink¹, Xiaozhong Liu, Joseph M Fox.

Abstract

A Cu-catalyzed method for coupling α-substituted-α-diazoesters with terminal alkynes to give substituted allenoates is described. Key to the development of a selective method was the recognition that an adventitous base catalyzes the isomerization to form the allenoate product. A plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.

Entities: Chemical

Mesh：

Substances：

Year: 2011 PMID： 21486078 PMCID： PMC3128944 DOI： 10.1021/ol2006242

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

1. Some typical advances in the synthetic applications of allenes.

Authors: Shengming Ma
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

2. Transition-metal-catalyzed rearrangement of allenyl sulfides: a route to furan derivatives.

Authors: Lingling Peng; Xiu Zhang; Ming Ma; Jianbo Wang
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Unexpected facile sequential halolactamization-hydroxylation of 2, 3-allenamides with CuX(2) for the efficient synthesis of 4-halo-5-hydroxypyrrol-2(5H)-ones.

Authors: S Ma; H Xie
Journal: Org Lett Date: 2000-11-30 Impact factor: 6.005

4. Enantioselective synthesis of allenic esters via an ylide route.

Authors: Chuan-Ying Li; Xiu-Li Sun; Qing Jing; Yong Tang
Journal: Chem Commun (Camb) Date: 2006-06-07 Impact factor: 6.222

5. Development of a new Lewis acid-catalyzed [3,3]-sigmatropic rearrangement: the allenoate-Claisen rearrangement.

Authors: Tristan H Lambert; David W C MacMillan
Journal: J Am Chem Soc Date: 2002-11-20 Impact factor: 15.419

6. Carbonylation of Alkynyl Epoxides: Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives.

Authors: Marcelo E. Piotti; Howard Alper
Journal: J Org Chem Date: 1997-11-28 Impact factor: 4.354

7. Transition metal-catalyzed/mediated reaction of allenes with a nucleophilic functionality connected to the alpha-carbon atom.

Authors: Shengming Ma
Journal: Acc Chem Res Date: 2003-09 Impact factor: 22.384

8. Beyond the aza-Morita-Baylis-Hillman reaction: Lewis base-catalyzed reactions of N-Boc-imines with ethyl 2,3-butadienoate.

Authors: Xiao-Yang Guan; Yin Wei; Min Shi
Journal: J Org Chem Date: 2009-08-21 Impact factor: 4.354

Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.

1. Some typical advances in the synthetic applications of allenes.

2. Transition-metal-catalyzed rearrangement of allenyl sulfides: a route to furan derivatives.

3. Unexpected facile sequential halolactamization-hydroxylation of 2, 3-allenamides with CuX(2) for the efficient synthesis of 4-halo-5-hydroxypyrrol-2(5H)-ones.

4. Enantioselective synthesis of allenic esters via an ylide route.

5. Development of a new Lewis acid-catalyzed [3,3]-sigmatropic rearrangement: the allenoate-Claisen rearrangement.

6. Carbonylation of Alkynyl Epoxides: Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives.

7. Transition metal-catalyzed/mediated reaction of allenes with a nucleophilic functionality connected to the alpha-carbon atom.

8. Beyond the aza-Morita-Baylis-Hillman reaction: Lewis base-catalyzed reactions of N-Boc-imines with ethyl 2,3-butadienoate.

9. An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

10. Direct and stereospecific synthesis of allenes via reduction of propargylic alcohols with Cp2Zr(H)Cl.

1. The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

Review 2. Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.

3. Phase-transfer-catalysed asymmetric synthesis of tetrasubstituted allenes.

4. A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds.