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Synthesis 2010(1): 161-170
DOI: 10.1055/s-0029-1217046
DOI: 10.1055/s-0029-1217046
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New YorkAsymmetric Diels-Alder Reactions of Vinylindoles Using Organocatalysis
Further Information
Received
28 July 2009
Publication Date:
19 October 2009 (online)
Publication History
Publication Date:
19 October 2009 (online)

Abstract
The different behavior of 3- and 2-vinylindoles in Diels-Alder cycloaddition reactions in the presence of bifunctional hydrogen bond donor organocatalysts is described.
Key words
asymmetric catalysis - Diels-Alder reactions - kinetic resolution - organocatalysis - vinylindoles
- 1a
Oppolzer W. In Comprehensive Organic Synthesis Vol. 5:Trost BM.Fleming I. Pergamon; Oxford: 1991. p.315 - 1b
Pindur U.Lutz G.Otto C. Chem. Rev. 1993, 93: 741 - For recent reviews, see:
- 2a
Nicolau KC.Snyder SA.Montagnon T.Vasilikogiannakis G. Angew. Chem. Int. Ed. 2002, 41: 1668 - 2b
Corey EJ. Angew. Chem. Int. Ed. 2002, 41: 1650 - 2c
Takao K.-i.Munakata R.Tadano K.-i. Chem. Rev. 2005, 105: 4779 - Reviews:
- 3a
Kagan HB.Riant O. Chem. Rev. 1992, 92: 1007 - 3b
Hayashi Y. In Cycloaddition Reactions in Organic SynthesisKobayashi S.Jørgensen KA. Wiley-VCH; Weinheim: 2001. p.5 - 3c
Evans DA.Johnson JS. In Comprehensive Asymmetric Catalysis Vol. 3:Jacobsen EN.Pfaltz A.Yamamoto H. Springer; New York: 1999. p.1177 - 3d
Reymond S.Cossy J. Chem. Rev. 2008, 108: 5359 - Representative examples:
- 3e
Sibi MP.Stanley LM.Jasperse CP. J. Am. Chem. Soc. 2005, 127: 8276 - 3f
Shirikawa S.Lombardi PJ.Leighton JL. J. Am. Chem. Soc. 2005, 127: 994 - 3g
Kano T.Hashimoto T.Maruoka K. J. Am. Chem. Soc. 2005, 127: 11926 - 3h
Cabrera S.Arrayas RG.Carretero JC. J. Am. Chem. Soc. 2005, 127: 16394 - 3i
Kano T.Hashimoto T.Maruoka K. J. Am. Chem. Soc. 2006, 128: 2174 - 4
Williams RM.Stocking EM. Angew. Chem. Int. Ed. 2003, 42: 3078 - 5a
Tarasow TM.Tarasow SL.Eaton BE. Nature 1997, 389: 54 - 5b
Seelig B.Jäschke A. Chem. Biol. 1999, 6: 167 - 6
Chandra M.Silverman SK. J. Am. Chem. Soc. 2008, 130: 2936 - 7a
Hilvert D.Hill KW.Nared KD.Auditor M.-T. J. Am. Chem. Soc. 1989, 111: 9261 - 7b
Braisted AC.Schultz PG. J. Am. Chem. Soc. 1990, 112: 7430 - 8
MacMillan DWC. Nature 2008, 455: 304 - 9a
Ahrendt KA.Borths CJ.MacMillan DWC. J. Am. Chem. Soc. 2000, 122: 4243 - 9b
Sakakura A.Suzuki K.Ishihara K. Adv. Synth. Catal. 2006, 348: 2457 ; and references therein - 10a
Schreiner PR.Wittkopp A. Org. Lett. 2002, 4: 217 - 10b
Wittkopp A.Schreiner PR. Chem. Eur. J. 2003, 9: 407 - 10c
Huang Y.Unni AK.Thadani AN.Rawal VH. Nature 2003, 424: 146 - 10d
Unni A.Takenaka N.Yamamoto H.Rawal VH. J. Am. Chem. Soc. 2005, 127: 1336 - 11
Jeffrey GA. An Introduction to Hydrogen Bonding Oxford University Press; New York: 1997. - 12a
Herrera PR.Sgarzani V.Bernardi L.Ricci A. Angew. Chem. Int. Ed. 2005, 44: 6576 - 12b
Fini F.Sgarzani V.Pettersen D.Herrera RP.Bernardi L.Ricci A. Angew. Chem. Int. Ed. 2005, 44: 7975 - 12c
Bernardi L.Fini F.Fochi M.Ricci A. Chimia 2007, 61: 224 ; and references therein - 12d
Marianacci O.Micheletti G.Bernardi L.Fini F.Fochi M.Pettersen D.Sgarzani V.Ricci A. Chem. Eur. J. 2007, 13: 8338 - 12e
Fini F.Micheletti G.Bernardi L.Pettersen D.Fochi M.Ricci A. Chem. Commun. 2008, 4345 - 13a
Wang Y.Li H.Wang Y.-Q.Liu Y.Foxman BM.Deng L. J. Am. Chem. Soc. 2007, 129: 6364 - 13b
Okamura H.Iwagawa T.Nakatani M. Tetrahedron Lett. 1995, 36: 5939 - 13c
Riant O.Kagan KB. Tetrahedron Lett. 1989, 30: 7403 - 13d
Shen J.Nguyen TT.Goh Y.-P.Ye W.Fu X.Tan C.-H. J. Am. Chem. Soc. 2006, 128: 13692 - 14
Gioia C.Hauville A.Bernardi L.Fini F.Ricci A. Angew. Chem. Int. Ed. 2008, 47: 9236 - 15
Pindur U.Lutz G.Fischer G.Schollmeyer D.Massa W.Schröder L. Tetrahedron 1993, 49: 2863 - Early examples:
- 16a
Noland WE.Kuryla WC.Lange RF. J. Am. Chem. Soc. 1959, 81: 6010 - 16b
Noland WE.Sundberg RJ. J. Org. Chem. 1963, 28: 884 - 16c
Bergamasco R.Porter QN.Yap C. Aust. J. Chem. 1977, 30: 1531 - 16d
Pfeuffer L.Pindur U. Helv. Chim. Acta 1988, 71: 467 - For reviews, see:
- 16e
Pindur U. Heterocycles 1998, 27: 1253 - 16f
Sundberg RJ. In Indoles Academic Press; London: 1996. p.156 - 16g
Blechert S.Knier R.Schroers H.Wirth T. Synthesis 1995, 592 - Recent examples:
- 16h
Bleile M.Otto H.-H. Monatsh. Chem. 2005, 136: 1799 - 16i
Bleile M.Wagner T.Otto H.-H. Helv. Chim. Acta 2005, 88: 2879 - 17
Padwa A.Lynch SM.Mejía-Oneto JM.Zhang H. J. Org. Chem. 2005, 70: 2206 ; and references therein - 18
Abbiati G.Canevari V.Facoetti D.Rossi E. Eur. J. Org. Chem. 2007, 517 ; and references therein - 19a
Schreiner PR. Chem. Soc. Rev. 2003, 289 - 19b
Takemoto Y. Org. Biomol. Chem. 2005, 3: 4299 - 19c
Taylor MS.Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 1520 - 19d
Doyle AG.Jacobsen EN. Chem. Rev. 2007, 107: 5713 - 19e
Pihko PM. Angew. Chem. Int. Ed. 2004, 43: 2062 - 19f
Palomo C.Oiarbide M.López R. Chem. Soc. Rev. 2009, 632 - 20
Noland WE.Xia G.-M.Gee KR.Konkel MJ.Wahlstrom MJ.Condoluci JJ.Rieger DL. Tetrahedron 1996, 52: 4555 - 21a
Vakulya B.Varga S.Csámpai A.Soós T. Org. Lett. 2005, 7: 1967 - 21b
Connon SJ. Chem. Commun. 2008, 2499 - 22
Pindur U.Kim M.-H.Rogge M.Massa W.Molinier M. J. Org. Chem. 1992, 57: 910 - 23
Itoh J.Fuchibe K.Akiyama T. Angew. Chem. Int. Ed. 2008, 47: 4016 - 24
Török B.Abid M.London G.Esquibel J.Török M.Mhadgut SC.Yan P.Prakash GKS. Angew. Chem. Int. Ed. 2005, 44: 3086 - 25a
Jia Y.-X.Zhong J.Zhu S.-F.Zhang C.-M.Zhou Q.-L. Angew. Chem. Int. Ed. 2007, 46: 5565 - 25b
Terada M.Sorimachi K. J. Am. Chem. Soc. 2007, 129: 292 - 25c
Wang Y.-Q.Song J.Hong R.Li H.Deng L. J. Am. Chem. Soc. 2006, 128: 8156 - 26a
Eitel M.Pindur UH. Synthesis 1989, 364 - 26b
Eitel M.Pindur UH. J. Org. Chem. 1990, 55: 5368 - 27a
Keith JM.Larrow JF.Jacobsen EN. Adv. Synth. Catal. 2001, 343: 5 - 27b
Kagan HB.Fiaud JC. Top. Stereochem. 1988, 18: 249 - Recent examples of enantio-enrichment of catalytic products through organocatalysis:
- 27c
Enders D.Narine AA.Toulgoat F.Bisschops T. Angew. Chem. Int. Ed. 2008, 47: 5661 - 27d
Akiyama T.Katoh T.Mori K. Angew. Chem. Int. Ed. 2009, 48: 4226 - 27e
Frisch K.Jørgensen KA. Org. Biomol. Chem. 2007, 5: 2966 - 28 During the review process, an organocatalytic
asymmetric Diels-Alder reaction of a 2-vinylindole derivative
was reported:
Jones SB.Simmons B.MacMillan DWC. J. Am. Chem. Soc. 2009, 131: 13606 - 29
Brunner H.Bügler J. Bull. Soc. Chim. Belg. 1997, 106: 77 - 30
Scott MS.Lucas AC.Luckhurst CA.Prodger JC.Dixon DJ. Org. Biomol. Chem. 2006, 4: 1313 - 31
Waser J.Gaspar B.Hisanori N.Carreira EN. J. Am. Chem. Soc. 2006, 128: 11693
References
Obtained from (R)-bornylamine and 1,1′-thiocarbonyl-diimidazole in THF, followed by chromatographic purification.