Highly selective synthesis of tetra-substituted furans and cyclopropenes: Copper(i)-catalyzed formal cycloadditions of internal aryl alkynes and diazoacetates

Organic and Biomolecular Chemistry

Volumn 10, Issue 37, 2012, Pages 7483-7486

  Swenson, Andrew K ^a   Higgins, Kate E ^a   Brewer, Matthew G ^a   Brennessel, William W ^b   Coleman, Michael G ^a  

^a ROCHESTER INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL ALKYNES; CHEMOSELECTIVE; CYCLOADDITIONS; CYCLOPROPENES; ELECTRON-RICH; ISOLATED YIELD; REGIOSELECTIVE SYNTHESIS; SELECTIVE SYNTHESIS;

AROMATIC COMPOUNDS; CATALYSIS; CYCLOADDITION; ORGANIC POLLUTANTS;

ACETYLENE;

ACETIC ACID DERIVATIVE; ALKYNE; AZO COMPOUND; COPPER; CYCLOPROPANE DERIVATIVE; CYCLOPROPENE; FURAN DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ACETATES; ALKYNES; AZO COMPOUNDS; CATALYSIS; COPPER; CYCLIZATION; CYCLOPROPANES; FURANS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

TETRA;

EID: 84865682630     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob26295a     Document Type: Article

References (32)

1. H. M. L. Davies K. R. Romines Direct synthesis of furans by 3 + 2 cycloadditions between rhodium(ii) acetate stabilized carbenoids and acetylenes Tetrahedron 1988 44 11 3343 3348
2. 4 catalyzed formation of fluorine-containing polysubstituted furans from diazo compounds and aromatic alkynes Tetrahedron 2010 66 6 1261 1266
3. L. Zhou J.-C. Ma Y. Zhang J.-B. Wang Copper-catalyzed cascade coupling/cyclization of terminal alkynes with diazoacetates: a straightforward route for trisubstituted furans Tetrahedron Lett. 2011 52 42 5484 5487
4. 4-n). Stereochemical heuristics for ligand exchange and catalyst synthesis J. Am. Chem. Soc. 2005 127 41 14223 14230 (Pubitemid 41457587)
5. E. J. Park S. H. Kim S. Chang Copper-catalyzed reaction of α-aryldiazoesters with terminal alkynes: a formal [3 + 2] cycloaddition route leading to indene derivatives J. Am. Chem. Soc. 2008 130 51 17268 17269
6. P. Panne J. M. Fox Rh-catalyzed intermolecular reactions of alkynes with α-diazoesters that possess β-hydrogens: ligand-based control over divergent pathways J. Am. Chem. Soc. 2007 129 1 22 23 (Pubitemid 46068247)
7. 4-catalyzed cyclopropenation of alkynes with styryldiazoacetates J. Am. Chem. Soc. 2010 132 48 17211 17215
8. P. Mueller N. Pautex M. P. Doyle V. Bagheri Rhodium(ii)-catalyzed isomerizations of cyclopropenes. Evidence for rhodium(ii)-complexed vinylcarbene intermediates Helv. Chim. Acta 1990 73 5 1233 1241
9. J. F. Briones H. M. L. Davies Silver triflate-catalyzed cyclopropenation of internal alkynes with donor-/acceptor-substituted diazo compounds Org. Lett. 2011 13 3984 3987
10. X. Cui X. Xu H. Lu S. Zhu L. Wojtas X. P. Zhang Enantioselective cyclopropenation of alkynes with acceptor-acceptor-substituted diazo reagents via Co(ii)-based metalloradical catalysis J. Am. Chem. Soc. 2011 133 10 3304 3307
11. M. Uehara H. Suematsu Y. Yasutomi T. Katsuki Enantioenriched synthesis of cyclopropenes with a quaternary stereocenter, versatile building blocks J. Am. Chem. Soc. 2011 133 2 170 171
12. M. L. Davies Huw H. Lee Gene Dirhodium(ii) tetra(N- (dodecylbenzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes Org. Lett. 2004 6 8 1233 1236
13. M. P. Doyle M. Protopopova P. Muller D. Ene E. A. Shapiro Effective uses of dirhodium(ii) tetrakis[methyl 2-oxopyrrolidine-5(R or S)-carboxylate] for highly enantioselective intermolecular cyclopropenation reactions J. Am. Chem. Soc. 1994 116 19 8492 8498 (Pubitemid 24981582)
14. M. P. Doyle D. G. Ene C. S. Peterson V. Lynch Macrocyclic cyclopropenes by highly enantioselective intramolecular addition of metal carbenes to alkynes Angew. Chem., Int. Ed. 1999 38 5 700 702 (Pubitemid 29129838)
15. M. P. Doyle T. M. Weathers, Jr. Y. Wang Stereoselectivity in metal carbene addition to a carbon-carbon triple bond tied to the reactant diazoacetate through a chiral linker Adv. Synth. Catal. 2006 348 16-17 2403 2409 (Pubitemid 44865619)
16. M. N. Protopopova M. P. Doyle P. Mueller D. Ene High enantioselectivity for intermolecular cyclopropenation of alkynes by diazo esters catalyzed by chiral dirhodium(ii) carboxamides J. Am. Chem. Soc. 1992 114 7 2755 2757
17. B. A. Keay Synthesis of multi-substituted furan rings: the role of silicon Chem. Soc. Rev. 1999 28 4 209 215
18. S. F. Kirsch Syntheses of polysubstituted furans: recent developments Org. Biomol. Chem. 2006 4 11 2076 2080 (Pubitemid 43829906)
19. H. N. C. Wong X.-L. Hou K.-S. Yeung H. Huang Five-membered heterocycles: furan Mod. Heterocycl. Chem. 2011 1 533 592
20. J. Salaun M. S. Baird Biologically active cyclopropanes and cyclopropenes Curr. Med. Chem. 1995 2 1 511 542
21. J. W. Huffman L. W. Padgett Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes Curr. Med. Chem. 2005 12 12 1395 1411 (Pubitemid 40872583)
22. E. G. Mamedov E. I. Klabunovskii Asymmetric Diels-Alder reactions of cyclopentadiene in the synthesis of chiral norbornene derivatives Russ. J. Org. Chem. 2008 44 8 1097 1120
23. M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, 1998, p. 652
24. H. M. L. Davies R. E. J. Beckwith Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion Chem. Rev. 2003 103 8 2861 2904
25. M. P. Doyle R. Duffy M. Ratnikov L. Zhou Catalytic carbene insertion into C-H bonds Chem. Rev. 2009 110 2 704 724
26. F. Gonzalez-Bobes M. D. B. Fenster S. Kiau L. Kolla S. Kolotuchin M. Soumeillant Rhodium-catalyzed cyclopropanation of alkenes with dimethyl diazomalonate Adv. Synth. Catal. 2008 350 6 813 816
27. 4- catalyzed asymmetric cyclopropenation of aryl alkynes Tetrahedron 2011 67 24 4313 4317
28. J. L. Thompson H. M. L. Davies Enhancement of cyclopropanation chemistry in the silver-catalyzed reactions of aryldiazoacetates J. Am. Chem. Soc. 2007 129 19 6090 6091 (Pubitemid 46786795)
29. J. F. Briones H. M. L. Davies Gold(i)-catalyzed asymmetric cyclopropenation of internal alkynes J. Am. Chem. Soc. 2012 134 29 11916 11919
30. H. M. L. Davies M. G. Coleman D. L. Ventura Balance between Allylic C-H activation and cyclopropanation in the reactions of donor-acceptor-substituted rhodium carbenoids with trans-alkenes Org. Lett. 2007 9 4971 4974
31. D. L. Ventura Z. Li M. G. Coleman H. M. L. Davies Intermolecular C-H functionalization versus cyclopropanation of electron rich 1,1-disubstituted and trisubstituted alkenes Tetrahedron 2009 65 3052 3061
32. M. Rubin M. Rubina V. Gevorgyan Transition metal chemistry of cyclopropenes and cyclopropanes Chem. Rev. 2007 107 7 3117 3179 (Pubitemid 47162906)