2,2,6-Trimethyl-4H-1,3-dioxin-4-one (TMD): A Versatile Acetylketene Equivalent
Fernando Henrique de Souza GamaDepartamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil.Email: Fernandogama@ufrj.br
Fernando Henrique de Souza Gama graduated in Technology of Natural Product Chemistry (2008) from the Instituto Federal de Educação, Ciência e Tecnologia do Rio de Janeiro, completed his M.Sc. in Chemistry at the Universidade Federal do Rio de Janeiro, and has begun his D.Sc. in Chemistry at the same university under the supervision of Professor Simon J. Garden. His research interests focus on the development of new synthetic one-pot methodologies and the synthesis of 1,3-dicarbonyl derivatives. |
Australian Journal of Chemistry 65(3) 299-300 https://doi.org/10.1071/CH12070
Submitted: 3 February 2012 Accepted: 8 February 2012 Published: 21 March 2012
References
[1] (a) W. Shumway, S. Ham, J. Moer, B. R. Whittlesey, D. M. Birney, J. Org. Chem. 2000, 65, 7731.| 1:CAS:528:DC%2BD3cXnsVaksbg%3D&md5=b45e1b9276e103b3f798e0663d2b52ddCAS |
(b) C. O. Kappe, M. W. Wong, C. Wentrup, J. Org. Chem. 1995, 60, 1686.
(c) C. Wentrup, W. Heilmaver, G. Kollenz, Synthesis 1994, 1219.
(d) G. Kollenz, S. Ebner, Science of Synthesis (Houben-Weyl) 2006, 23, 271 .(Georg Thieme Verlag KG: Stuttgart).
[2] M. F. Carroll, A. R. Bader, J. Am. Chem. Soc. 1953, 75, 5400.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG2MXkvV2k&md5=0e15f8d9ebc99906228522c2f1205a4cCAS |
[3] (a) K. Bell, D. V. Sadasivam, I. R. Gudipati, H. Ji, D. Birney, Tetrahedron Lett. 2009, 50, 1295.
| 1:CAS:528:DC%2BD1MXhs1Ogsbs%3D&md5=be2b82d529ffb2791c1740753df4fde9CAS |
(b) A. E. May, T. R. Hoye, J. Org. Chem. 2010, 75, 6054.
[4] V. Sridharan, M. Ruiz, J. C. Menéndez, Synthesis 2010, 1053.
| 1:CAS:528:DC%2BC3cXltVCrtr4%3D&md5=be50581a90639e9ccdc4ea0bbe89deb7CAS |
[5] Y. Gan, L. M. Harwood, S. C. Richards, I. E. D. Smih, V. Vinader, Tetrahedron: Asymmetry 2009, 20, 723.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmtVejurk%3D&md5=0e95557f7977f11f57ff43b4d2bc17eaCAS |
[6] M. T. Huggins, P. S. Barber, D. Florian, W. Howton, Synth. Commun. 2008, 38, 4226.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlals7%2FL&md5=258fdeaa868bab31b4310d65f39b8df7CAS |
[7] J. Wang, B. Stefane, D. Jaber, J. A. I. Smith, C. Vickery, M. Diop, H. O. Sintim, Angew. Chem. Int. Ed. 2010, 49, 3964.
| 1:CAS:528:DC%2BC3cXmsVOgur4%3D&md5=ab588444d966456dff2d548a09c4eb96CAS |
[8] E. J. Roh, J. M. Keller, Z. Olah, M. J. Iadarola, K. A. Jacobson, Bioorg. Med. Chem. 2008, 16, 9349.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1ens7rK&md5=b55f76f39c8757e95b143cc7d5df2791CAS |
[9] M. Sato, N. Kanuma, T. Kato, Chem. Pharm. Bull. (Tokyo) 1982, 30, 1315.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XksFGktrs%3D&md5=bb7c7bc431e1330a3f1524beb630cf97CAS |
[10] M. Xia, Y.-G. Wang, Synthesis 2003, 262.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtlOks7o%3D&md5=8622ce11e017c46891cf23b28e870c65CAS |
[11] A. S. Vieira, R. L. O. R. Cunha, C. F. Klitzke, J. Zukerman-Schpector, H. A. Stefani, Tetrahedron 2010, 66, 773.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFGnu7vM&md5=ee434b5544f10413a25b800c84146d59CAS |
[12] C. Audouard, K. Bettaney, C. T. Doan, G. Rinaudi, P. J. Jervis, J. M. Percy, Org. Biomol. Chem. 2009, 7, 1573.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjvFKqsr8%3D&md5=ec90f097712a4affdd0fe8dd63d35fb3CAS |
[13] C. Bengtsson, F. Almqvist, J. Org. Chem. 2010, 75, 972.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFyqu7vL&md5=07810c63a9049f4d1a19e8420561bf31CAS |
[14] U. Jahn, P. Hartmann, I. Dix, P. G. Jones, Eur. J. Org. Chem. 2002, 718.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhsFSkt7Y%3D&md5=8c28a4e6bf7a6e3f2643d671fcdff208CAS |
[15] U. Jahn, E. Dinca, J. Org. Chem. 2010, 75, 4480.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntF2jtbY%3D&md5=9c7f0aa71bf3055992978ea8f926e682CAS |
[16] M. Peuchmaur, N. Saidani, C. Botte, E. Marechal, H. Vial, Y.-S. Wong, J. Med. Chem. 2008, 51, 4870.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXptl2hurw%3D&md5=ec0b45d51e19b8a815df218176adf024CAS |
[17] (a) A. Fettes, E. M. Carreira, J. Org. Chem. 2003, 68, 9274..
| 1:CAS:528:DC%2BD3sXosFWlsrY%3D&md5=9aedb9ed5180958e4bc094078ecf6903CAS |
(b) J Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837.
[18] T. J. Simpson, F. Soulas, C. L. Willis, Synlett. 2008, 2196.
| 1:CAS:528:DC%2BD1cXhtFKgs7nE&md5=d84c8d64cc10b99cea2ae265767e9d59CAS |
[19] M. Sato, J.-I. Sakaki, K. Takayama, S. Kobayashi, M. Suzuki, C. Kaneko, Chem. Pharm. Bull. (Tokyo) 1990, 38, 94.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXkvFOgsbY%3D&md5=2c06f2afe40fe2ea16c7cb3840058a54CAS |
[20] C. K. Skepper, D. S. Dalisay, T. F. Molinski, Bioorg. Med. Chem. Lett. 2010, 20, 2029.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXivFGksrw%3D&md5=f7a2d8440447400139f6f9cd39eb8d72CAS |