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Synthesis 2011(20): 3359-3363
DOI: 10.1055/s-0030-1260185
DOI: 10.1055/s-0030-1260185
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkWittig Olefination of Trifluoromethyl Ketones and Allylic Carbonates Mediated by Phosphines
Further Information
Received
20 June 2011
Publication Date:
24 August 2011 (online)
Publication History
Publication Date:
24 August 2011 (online)
Abstract
The Wittig olefination of trifluromethyl ketones and allylic carbonates mediated by tributylphosphine was realized to give corresponding trifluoromethyl dienes in good yields with excellent E-selectivities.
Key words
Wittig - trifluoromethyl ketones - trifluoromethyl olefins - ylides - allylic carbonate
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DOI: 10.4125/pd0015th:
- Primary Data (ZIP)
- 1
Maryanoff BE.Reitz AB. Chem. Rev. 1989, 89: 863 - 2a
Zhang C.Lu X. J. Org. Chem. 1995, 60: 2906Reference Ris Wihthout Link - 2b
Lu X.Lu Z.Zhang X. Tetrahedron 2006, 62: 457Reference Ris Wihthout Link - 2c
Lu Z.Lu X. Tetrahedron Lett. 1997, 38: 3461Reference Ris Wihthout Link - For reviews, see:
- 2d
Lu X.Zhang C.Xu Z. Acc. Chem. Res. 2001, 34: 535Reference Ris Wihthout Link - 2e
Methot JL.Roush WR. Adv. Synth. Catal. 2004, 346: 1035Reference Ris Wihthout Link - 2f
Lu X.Du Y.Lu C. Pure Appl. Chem. 2005, 77: 1985Reference Ris Wihthout Link - 2g
Nair V.Menon RS.Sreekanth AR.Abhilash N.Biju AT. Acc. Chem. Res. 2006, 39: 520Reference Ris Wihthout Link - 2h
Ye L.-W.Zhou J.Tang Y. Chem. Soc. Rev. 2008, 37: 1140Reference Ris Wihthout Link - 2i
Cowen BJ.Miller SJ. Chem. Soc. Rev. 2009, 38: 3102Reference Ris Wihthout Link - 2j
Marinetti A.Voituriez A. Synlett 2010, 174Reference Ris Wihthout Link - 3
Du Y.Lu X.Zhang C. Angew. Chem. Int. Ed. 2003, 42: 1035 - The group of Krische has used this class of compound as effective allylic alkylating agents, see:
- 4a
Cho C.-W.Krische M. Angew. Chem. Int. Ed. 2004, 43: 6689Reference Ris Wihthout Link - 4b
Cho C.-W.Kong J.-R.Krische M. Org. Lett. 2004, 6: 1337Reference Ris Wihthout Link - 4c
Park H.Cho C.-W.Krische M.Jiang Y.-Q.Shi Y.-L.Shi M. J. Am. Chem. Soc. 2008, 130: 7202Reference Ris Wihthout Link - 5a
Feng J.Lu X.Kong A.Han X. Tetrahedron 2007, 63: 6035Reference Ris Wihthout Link - 5b
Tan B.Candeias NR.Barbas CF. J. Am. Chem. Soc. 2011, 133: 4672Reference Ris Wihthout Link - 5c
Deng H.-P.Wei Y.Shi M. Org. Lett. 2011, 13: 3348Reference Ris Wihthout Link - For intramolecular, see:
- 5d
Ye L.-W.Sun X.-L.Wang Q.-G.Tang Y. Angew. Chem. Int. Ed. 2007, 46: 5951Reference Ris Wihthout Link - 5e
Wang Q.-G.Zhu S.-F.Ye L.-W.Zhou C.-Y.Sun X.-L.Tang Y.Zhou Q.-L. Adv. Synth. Catal. 2010, 352: 1914Reference Ris Wihthout Link - 5f
Han X.Ye L.-W.Sun X.-L.Tang Y. J. Org. Chem. 2009, 74: 3394Reference Ris Wihthout Link - 6
Zheng S.Lu X. Org. Lett. 2008, 10: 4481 - 7
Zheng S.Lu X. Org. Lett. 2009, 11: 3978 - 8
Du Y.Feng J.Lu X. Org. Lett. 2005, 7: 1987 - 9a
Chen Z.Zhang J. Chem. Asian J. 2010, 5: 1542Reference Ris Wihthout Link - 9b
Xie P.Huang Y.Chen R. Org. Lett. 2010, 12: 3768Reference Ris Wihthout Link - 9c
Zhou R.Wang J.Song H.He Z. Org. Lett. 2011, 13: 580Reference Ris Wihthout Link - 9d
Tian J.Zhou R.Sun H.Song H.He Z. J. Org. Chem. 2011, 76: 2374Reference Ris Wihthout Link - 10
Zhou R.Wang C.Song H.He Z. Org. Lett. 2010, 12: 976 - 11a
Wang T.Ye S. Org. Lett. 2010, 12: 4168Reference Ris Wihthout Link - 11b
Wang T.Ye S. Org. Biomol. Chem. 2011, 9: 5260Reference Ris Wihthout Link - 12a
Zhu X.-F.Henry CE.Wang J.Dudding T.Kwon O. Org. Lett. 2005, 7: 1387Reference Ris Wihthout Link - 12b
Zhu X.-F.Schaffner A.-P.Li RC.Kwon O. Org. Lett. 2005, 7: 2977Reference Ris Wihthout Link - 12c
Creech GS.Kwon O. Org. Lett. 2008, 10: 429Reference Ris Wihthout Link - 12d
Creech GS.Zhu X.-F.Fonovic B.Dudding T.Kwon O. Tetrahedron 2008, 64: 6935Reference Ris Wihthout Link - For selected synthesis of heterocycles containing a trifluoromethyl group, see:
- 13a
Burstein C.Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205Reference Ris Wihthout Link - 13b
Abid M.Torok B. Adv. Synth. Catal. 2005, 347: 1797Reference Ris Wihthout Link - 13c
Zhu J.Cheng Z.Xie H.Li S.Wu Y. Org. Lett. 2010, 12: 2434Reference Ris Wihthout Link - 13d
Morandi B.Carreira EM. Angew. Chem. Int. Ed. 2010, 49: 4294Reference Ris Wihthout Link - 13e
Matoba K.Kawai H.Furukawa T.Kusuda A.Tokunaga E.Nakaura S.Shiro M.Shibata N. Angew. Chem. Int. Ed. 2010, 49: 5762Reference Ris Wihthout Link - 13f
Kobatake T.Fujino D.Yoshida S.Yorimitsu H.Oshima K. J. Am. Chem. Soc. 2010, 132: 11838Reference Ris Wihthout Link - 13g
Jiang H.Wang Y.Wan W.Hao J. Tetrahedron 2010, 66: 2746Reference Ris Wihthout Link - For reviews, see:
- 13h
Ma J.-A.Cahard D. Chem. Rev. 2008, 108: PR1Reference Ris Wihthout Link - 13i
Nie J.Guo H.-C.Cahard D.Ma J.-A. Chem. Rev. 2011, 111: 455Reference Ris Wihthout Link - 14a
Basavaiah D.Reddy BS.Badsara SS. Chem. Rev. 2010, 110: 5447Reference Ris Wihthout Link - 14b
Basavaiah D.Rao AJ.Satyanarayana T. Chem. Rev. 2003, 103: 811Reference Ris Wihthout Link - For the synthesis and application of olefins with the trifluoromethyl group, see:
- 15a
Shimojuh N.Imura Y.Moriyama K.Togo H. Tetrahedron 2011, 67: 951Reference Ris Wihthout Link - 15b
Pedro MF.Hirner S.Kühn FE. Tetrahedron Lett. 2005, 46: 7777Reference Ris Wihthout Link - 15c
Chen Y.Huang L.Zhang XP. J. Org. Chem. 2003, 68: 5925Reference Ris Wihthout Link - 15d
Lebel H.Paquet V. Org. Lett. 2002, 4: 1671Reference Ris Wihthout Link - 15e
Nader BS.Cordova JA.Karen E.Reese KE.Powell CL. J. Org. Chem. 1994, 59: 2898Reference Ris Wihthout Link - 15f
Eguchi T.Aoyama T.Kakinuma K. Tetrahedron Lett. 1992, 33: 5545Reference Ris Wihthout Link