Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2008(23): 3869-3873
DOI: 10.1055/s-0028-1083217
DOI: 10.1055/s-0028-1083217
PSP
© Georg Thieme Verlag
Stuttgart ˙ New YorkRuthenium-Catalyzed Enantioselective Propargylation of Indoles with Propargylic Alcohols
Further Information
Received
28 July 2008
Publication Date:
06 November 2008 (online)
Publication History
Publication Date:
06 November 2008 (online)
Abstract
Ruthenium-catalyzed enantioselective propargylation of 1-(triisopropylsilyl)-1H-indoles with propargylic alcohols gives the corresponding β-propargylated indoles in good yields with high enantioselectivity. Reactions with 1-(1-naphthyl)prop-2-yn-1-ol achieve the highest enantioselectivity (up to 95% ee).
Key words
asymmetric synthesis - Friedel-Crafts alkylation - ruthenium - indoles - propargylic alcohols
- For recent reviews, see:
- 1a
Jørgensen KA. Synthesis 2003, 1117Reference Ris Wihthout Link - 1b
Bandini M.Melloni A.Umani-Ronchi A. Angew. Chem. Int. Ed. 2004, 43: 550Reference Ris Wihthout Link - 1c
Bandini M.Emer E.Tommasi S.Umani-Ronchi A. Eur. J. Org. Chem. 2006, 3527Reference Ris Wihthout Link - 1d
Poulsen TB.Jørgensen KA. Chem. Rev. 2008, 108: 2903Reference Ris Wihthout Link - For recent examples of asymmetric Friedel-Crafts alkylation of indole derivatives, see:
- 2a
Li C.-F.Liu H.Liao J.Cao Y.-J.Liu X.-P.Xiao W.-J. Org. Lett. 2007, 9: 1847Reference Ris Wihthout Link - 2b
Yang H.Hong Y.-T.Kim S. Org. Lett. 2007, 9: 2281Reference Ris Wihthout Link - 2c
Terada M.Sorimachi K. J. Am. Chem. Soc. 2007, 129: 292Reference Ris Wihthout Link - 2d
Kang Q.Zhao Z.-A.You S.-L. J. Am. Chem. Soc. 2007, 129: 1484Reference Ris Wihthout Link - 2e
Dong H.-M.Lu H.-H.Lu L.-Q.Chen C.-B.Xiao W.-J. Adv. Synth. Catal. 2007, 349: 1597Reference Ris Wihthout Link - 2f
Terada M.Yokoyama S.Sorimachi K.Uraguchi D. Adv. Synth. Catal. 2007, 349: 1863Reference Ris Wihthout Link - 2g
Jia Y.-X.Zhong J.Zhu S.-F.Zhang C.-M.Zhou Q.-L. Angew. Chem. Int. Ed. 2007, 46: 5565Reference Ris Wihthout Link - 2h
Evans DA.Fandrick KR.Song H.-J.Scheidt KA.Xu R. J. Am. Chem. Soc. 2007, 129: 10029Reference Ris Wihthout Link - 2i
Itoh J.Fuchibe K.Akiyama T. Angew. Chem. Int. Ed. 2008, 47: 4016Reference Ris Wihthout Link - 2j
Desimoni G.Faita G.Toscanini M.Boiocchi M. Chem. Eur. J. 2008, 14: 3630Reference Ris Wihthout Link - 2k
Liu H.Lu S.-F.Xu J.Du D.-M. Chem. Asian J. 2008, 3: 1111Reference Ris Wihthout Link - 2l
Zhang G.-W.Wang L.Nie J.Ma J.-A. Adv. Synth. Catal. 2008, 350: 1457Reference Ris Wihthout Link - 2m
Wanner MJ.Hauwert P.Schoemaker HE.de Gelder R.van Maarseveen JH.Hiemstra H. Eur. J. Org. Chem. 2008, 180Reference Ris Wihthout Link - 2n
Nakamura S.Hyodo K.Nakamura Y.Shibata T.Toru T. Adv. Synth. Catal. 2008, 350: 1443Reference Ris Wihthout Link - 2o
Abid M.Teixeira L.Török B. Org. Lett. 2008, 10: 933Reference Ris Wihthout Link - 2p
Liu W.-B.He H.Dai L.-X.You S.-L. Org. Lett. 2008, 10: 1815Reference Ris Wihthout Link - 2q
Yuan Z.-L.Lei Z.-Y.Shi M. Tetrahedron: Asymmetry 2008, 19: 1339Reference Ris Wihthout Link - 3
Inada Y.Nishibayashi Y.Uemura S. Angew. Chem. Int. Ed. 2005, 44: 7715 - 4
Matsuzawa H.Miyake Y.Nishibayashi Y. Angew. Chem. Int. Ed. 2007, 46: 6488 - 5
Matsuzawa H.Kanao K.Miyake Y.Nishibayashi Y. Org. Lett. 2007, 9: 5561 ; and supplementary information - 6
Nishibayashi Y.Milton MD.Inada Y.Yoshikawa M.Wakiji I.Hidai M.Uemura S. Chem. Eur. J. 2005, 11: 1433 - 7
Beswick PJ.Greenwood CS.Mowlem TJ.Nechvatal G.Widdowson DA. Tetrahedron 1988, 44: 7325