Diamidocarbenes as versatile and reversible [2+1] cycloaddition reagents

Nature Chemistry

Volumn 4, Issue 4, 2012, Pages 275-280

  Moerdyk, Jonathan P ^a   Bielawski, Christopher W ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; CARBENE; CYCLOPROPANE DERIVATIVE; DRUG DERIVATIVE; EPOXIDE; KETONE; METHANE;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; ALKENES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOPROPANES; EPOXY COMPOUNDS; KETONES; METHANE; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84858757444     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1267     Document Type: Article

References (50)

1. Reissig, H-U. & Zimmer, R. Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis. Chem. Rev. 103, 1151-1196 (2003).
2. McGarrigle, E. M. & Gilheany, D. G. Chromium-and manganese-salen promoted epoxidation of alkenes. Chem. Rev. 105, 1563-1602 (2005).
3. Carson, C. A. & Kerr, M. A. Heterocycles from cyclopropanes: applications in natural product synthesis. Chem. Soc. Rev. 38, 3051-3060 (2009).
4. Wessjohann, L. A. & Brandt, W. Biosynthesis and metabolism of cyclopropane rings in natural products. Chem. Rev. 103, 1625-1647 (2003).
5. Marco-Contelles, J., Molina, M. T. & Anjum, S. Naturally occurring cyclohexane epoxides: sources, biological activities, and synthesis. Chem. Rev. 104, 2857-2899 (2004).
6. Rademacher, P. Photoelectron spectra of cyclopropane and cyclopropene compounds. Chem. Rev. 103, 933-975 (2003).
7. Herges, R. Topology in chemistry: designing Möbius molecules. Chem. Rev. 106, 4820-4842 (2006).
8. Lebel, H., Marcoux, J-F., Molinaro, C. & Charette, A. B. Stereoselective cyclopropanation reactions. Chem. Rev. 103, 977-1050 (2003).
9. Pellissier, H. Recent developments in asymmetric cyclopropanation. Tetrahedron 64, 7041-7095 (2008).
10. Moss, R. A. in Carbene Chemistry (ed. Bertrand, G.) 57-101 (Marcel Dekker, 2002).
11. Jones, M. Jr & Moss, R. A. in Reactive Intermediate Chemistry (eds Moss, R. A., Platz, M. S. & Jones, M. Jr) Ch. 7, 273-328 (Wiley-Interscience, 2004).
12. Cheng, Y. & Meth-Cohn, O. Heterocycles derived from heteroatom-substituted carbenes. Chem. Rev. 104, 2507-2530 (2004).
13. Wang, J., Burdzinski, G., Kubicki, J. & Platz, M. S. Ultrafast UV-vis and IR studies of p-biphenylyl acetyl and carbomethoxy carbenes. J. Am. Chem. Soc. 130, 11195-11209 (2008).
14. Zhang, Y., Kubicki, J. & Platz, M. S. Ultrafast UV-visible and infrared spectroscopic observation of a singlet vinylcarbene and the intramolecular cyclopropenation reaction. J. Am. Chem. Soc. 131, 13602-13603 (2009).
15. Baceiredo, A., Bertrand, G. & Sicard, G. Synthesis of the first a-diazo phosphines. Phosphorous-carbon multiple-bond character of phosphinocarbenes. J. Am. Chem. Soc. 107, 4781-4783 (1985).
16. Igau, A., Baceiredo, A., Trinquier, G. & Bertrand, G. Bis(diisopropylamino)phosphinotrimethylsilylcarbene: a stable nucleophilic carbene. Angew. Chem. Int. Ed. 28, 621-622 (1989).
17. Khramov, D. M., Rosen, E. L., Lynch, V. M. & Bielawski, C. W. Diaminocarbene3ferrocenophanes and their transition-metal complexes. Angew. Chem. Int. Ed. 47, 2267-2270 (2008).
18. Lavallo, V. et al. Synthesis, reactivity, and ligand properties of a stable alkyl carbene. J. Am. Chem. Soc. 126, 8670-8671 (2004).
19. Siemeling, U. et al. N-heterocyclic carbenes which readily add ammonia, carbon monoxide and other small molecules. Chem. Sci. 1, 697-704 (2010).
20. Vignolle, J., Cattoën, X. & Bourissou, D. Stable noncyclic singlet carbenes. Chem. Rev. 109, 3333-3384 (2009).
21. Dröge, T. & Glorius, F. The measure of all rings-N-heterocyclic carbenes. Angew. Chem. Int. Ed. 49, 6940-6952 (2010).
22. Melami, M., Soleilhavoup, M. & Bertrand, G. Stable cyclic carbenes and related species beyond diaminocarbenes. Angew. Chem. Int. Ed. 49, 8810-8849 (2010).
23. Martin, D., Soleilhavoup, M. & Bertrand, G. Stable singlet carbenes as mimics for transition metal centers. Chem. Sci. 2, 389-399 (2011).
24. Enders, D. et al. Preparation, structure, and reactivity of 1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene, a new stable carbene. Angew. Chem. Int. Ed. 34, 1021-1023 (1995).
25. Goumri-Magnet, S., Kato, T., Gornitzka, H., Baceiredo, A. & Bertrand, G. Stereoselectivity and stereospecificity of cyclopropanation reactions with stable (phosphanyl)(silyl)carbenes. J. Am. Chem. Soc. 122, 4464-4470 (2000).
26. Krysiak, J. et al. The first asymmetric cyclopropanation reactions involving a stable carbene. J. Org. Chem. 66, 8240-8242 (2001).
27. Krysiak, J. et al. Stable optically pure phosphino(silyl)carbenes: reagents for highly enantioselective cyclopropanation reactions. Chem. Eur. J. 10, 1982-1986 (2004).
28. Martin, D. et al. Theoretical and experimental investigation of the basicity of phosphino(silyl)carbenes. J. Org. Chem. 70, 5671-5677 (2005).
29. Illa, O., Alvarez-Larena, A., Baceiredo, A., Branchadell, V. & Ortuño, R. M. Highly stereoselective and easy synthesis of enantiopure phosphoranyl oxiranes. Tetrahedron: Asymmetry 18, 2617-2620 (2007).
30. Illa, O., Bagan, X., Baceiredo, A., Branchadell, V. & Ortuño, R. M. Understanding the p-facial diastereoselectivity in the addition of chiral diaminophosphino(silyl)carbenes to activated olefins. Tetrahedron: Asymmetry 19, 2353-2358 (2008).
31. ′- diamidocarbene: studies in C-H insertion, reversible carbonylation, and transition-metal coordination chemistry. J. Am. Chem. Soc. 131, 16039-16041 (2009).
32. César, V., Lugan, N. & Lavigne, G. Reprogramming of a malonic N-heterocyclic carbene: a simple backbone modification with dramatic consequences on the ligand's donor properties. Eur. J. Inorg. Chem. 361-365 (2010).
33. ′-diamidoketenimines via coupling of isocyanides to an N-heterocyclic carbene. J. Org. Chem. 75, 2763-2766 (2010).
34. ′-diamidocarbene. Chem. Commun. 46, 4288-4290 (2010).
35. Braun, M., Frank, W., Reiss, G. J. & Ganter, C. An N-heterocyclic carbene with an oxalamide backbone. Organometallics 29, 4418-4420 (2010).
36. Hobbs, M. G. et al. The influence of electron delocalization upon the stability and structure of potential N-heterocyclic carbene precursors with 1,3-diaryl-imidazolidine-4,5-dione skeletons. New J. Chem. 34, 1295-1308 (2010).
37. ′-diamidocarbene. Organometallics 29, 4569-4578 (2010).
38. ′-diamidocarbenes. Organometallics 30, 2278-2284 (2011).
39. Wasserman, H. H., Clark, G. M. & Turley, P. C. Recent aspects of cyclopropanone chemistry. Top. Curr. Chem. 47, 73-156 (1974).
40. Olah, G. A. & Molnar, A. In Hydrocarbon Chemistry (ed. Lagowski, J. J.) Ch. 7, 371-395 (Wiley-Interscience, 2003).
41. Linstead, R. P. & Whalley, M. Conjugated macrocycles. Part XXII. Tetrazaporphin and its metallic derivatives. J. Chem. Soc. 4839-4846 (1952).
42. Moss, R. A. & Huselton, J. K. Dimethoxycarbene: stereospecificity in the additions of a nucleophilic carbene to b-deuteriostyrenes. J. Chem. Soc. Chem. Commun. 950-951 (1976).
43. Mendez, F. & Garcia-Garibay, M. A. A hard-soft acid-base and DFT analysis of singlet-triplet gaps and the addition of singlet carbenes to alkenes. J. Org. Chem. 64, 7061-7066 (1999).
44. Lecea, B. et al. Theoretical study on the mechanism of the 2φ1 thermal cycloaddition between alkenes and stable singlet (phosphino)(silyl) carbenes. J. Org. Chem. 72, 357-366 (2007).
45. Mukai, T., Nakazawa, T. & Isobe, K. Thermal decomposition of troponetosylhydrazone. Tetrahedron Lett. 565-569 (1968).
46. Jones, W. M., Hamon, B. N., Joines, R. C. & Ennis, C. L. Stereochemistry of the addition of cycloheptatrienylidene to electron deficient double bonds. Tetrahedron Lett. 3909-3912 (1969).
47. Hamaguchi, M., Matsubara, H. & Nagai, T. Reaction of vinylcarbenoids with benzaldehydes: formation of vinylcarbonyl ylides followed by ring closure to oxiranes and dihydrofurans. J. Org. Chem. 66, 5395-5404 (2001).
48. Dolbier, W. R. Jr & Battiste, M. A. Structure, synthesis, and chemical reactions of fluorinated cyclopropanes and cyclopropenes. Chem. Rev. 103, 1071-1098 (2003).
49. Lehn, J-M. From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry. Chem. Soc. Rev. 36, 151-160 (2007).
50. Hunt, R. A. R. & Otto, S. Dynamic combinatorial libraries: new opportunities in systems chemistry. Chem. Commun. 47, 847-858 (2011).