RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2013; 45(1): 1-16
DOI: 10.1055/s-0032-1317575
DOI: 10.1055/s-0032-1317575
review
Recent Advances in Phenol Dearomatization and Its Application in Complex Syntheses
Weitere Informationen
Publikationsverlauf
Received: 15. September 2012
Accepted after revision: 22. Oktober 2012
Publikationsdatum:
07. November 2012 (online)
Abstract
As a powerful tool, the dearomatization of phenols has been explored extensively and utilized by organic chemists during the course of complex syntheses. This review highlights recent advances in phenol dearomatizations, especially those accomplished in an enantioselective manner, and the application of dearomatization strategies in complex syntheses.
1 Introduction
2 New Developments in Phenol Dearomatization
3 Enantioselective Phenol Dearomatization
3.1 Controlled by Chiral Substrate
3.2 Controlled by Chiral Catalyst
3.3 Controlled by Chiral Hypervalent Iodine
4 Enantioselective Phenol Dearomatization Strategies in Complex Syntheses
4.1 With the Formation of a Carbon–Oxygen Bond
4.2 With the Formation of a Carbon–Carbon Bond
4.3 With the Formation of a Carbon–Nitrogen Bond
5 Conclusion
-
References
- 1a Wender PA, Handy ST, Wright DL. Chem. Ind. 1997; 765: 767
- 1b Gaich T, Baran PS. J. Org. Chem. 2010; 75: 4657
- 2a Bach T. Angew. Chem. Int. Ed. 1996; 35: 729
- 2b Quideau S, Pouységu L. Org. Prep. Proced. Int. 1999; 31: 617
- 2c Pape AR, Kaliappan KP, Kündig EP. Chem. Rev. 2000; 100: 2917
- 2d Magdziak D, Meek SJ, Pettus TR. R. Chem. Rev. 2004; 104: 1383
- 2e Keane JM, Harman WD. Organometallics 2005; 24: 1786
- 2f López Ortiz F, Iglesias MJ, Fernández I, Andújar Sánchez CM, Gómez GR. Chem. Rev. 2007; 107: 1580
- 2g Quideau S, Pouységu L, Deffieux D. Synlett 2008; 467
- 2h Pouységu L, Deffieux D, Quideau S. Tetrahedron 2010; 66: 2235
- 2i Roche SP, Porco Jr JA. Angew. Chem. Int. Ed. 2011; 50: 4068
- 3 Pelter A, Elgendy SM. A. J. Chem. Soc., Perkin Trans. 1 1993; 1891
- 4a McKillop A, McLaren L, Taylor RJ. K. J. Chem. Soc., Perkin Trans. 1 1994; 2047
- 4b Felpin F-X. Tetrahedron Lett. 2007; 48: 409
- 5a Pouységu L, Chassaing S, Dejugnac D, Lamidey A.-M, Miqueu K, Sotiropoulos J.-M, Quideau S. Angew. Chem. Int. Ed. 2008; 47: 3552
- 5b Mitchell AS, Russell RA. Tetrahedron Lett. 1993; 34: 545
- 5c Lion CJ, Vasselin DA, Schwalbe CH, Matthews CS, Stevens MF. G, Westwell AD. Org. Biomol. Chem. 2005; 3: 3996
- 5d Quideau S, Pouysegu L, Deffieux D, Ozanne A, Gagnepain J, Fabre I, Oxoby M. ARKIVOC 2003; (vi): 106
- 6 Karam O, Martin A, Jouannetaud M.-P, Jacquesy J.-C. Tetrahedron Lett. 1999; 40: 4183
- 7a Wipf P, Kim Y, Fritch PC. J. Org. Chem. 1993; 58: 7195
- 7b Quideau S, Looney MA, Pouységu L, Ham S, Birney DM. Tetrahedron Lett. 1999; 40: 615
- 8a Kita Y, Tohma H, Kikuchi K, Inagaki M, Yakura T. J. Org. Chem. 1991; 56: 435
- 8b Liang H, Ciufolini MA. Chem.–Eur. J. 2010; 16: 13262
- 9 Murakata M, Yamada K, Hoshino O. Chem. Commun. 1994; 443
- 10a Kita Y, Tohma H, Inagaki M, Hatanaka K, Yakura T. J. Am. Chem. Soc. 1992; 114: 2175
- 10b Berard D, Giroux M.-A, Racicot L, Sabot C, Canesi S. Tetrahedron 2008; 64: 7537
- 11 Guérard KC, Chapelle C, Giroux M.-A, Sabot C, Beaulieu M.-A, Achache N, Canesi S. Org. Lett. 2009; 11: 4756
- 12 Guérard KC, Sabot C, Beaulieu M.-A, Giroux M.-A, Canesi S. Tetrahedron 2010; 66: 5893
- 13 Sabot C, Commare B, Duceppe MA, Nahi S, Guérard KC, Canesi S. Synlett 2008; 3226
- 14 Quideau S, Looney MA, Pouységu L. Org. Lett. 1999; 1: 1651
- 15 Desjardins S, Andrez J.-C, Canesi S. Org. Lett. 2011; 13: 3406
- 16 Gloer JB, Rinderknecht BL, Wicklow DT, Dowd PF. J. Org. Chem. 1989; 54: 2530
- 17 Puri A, Saxena R, Saxena RP, Saxena KC, Srivastava V, Tandon JS. J. Nat. Prod. 1993; 56: 995
- 18 Nicolaou KC, Roecker AJ, Follmann M, Baati R. Angew. Chem. Int. Ed. 2002; 41: 2107
- 19 Jacquemot G, Canesi S. J. Org. Chem. 2012; 77: 7588
- 20 Dohi T, Nakae T, Ishikado Y, Kato D, Kita Y. Org. Biomol. Chem. 2011; 9: 6899
- 21a Ochiai M, Sumi K, Takaoka Y, Kunishima M, Nagao Y, Shiro M, Fujita E. Tetrahedron 1988; 44: 4095
- 21b Chen J.-M, Huang X. Synlett 2004; 552
- 21c Yan J, Jin H, Chen Z. J. Chem. Res. 2007; 233
-
22 Liang J, Chen J, Du F, Zeng X, Li L, Zhang H. Org. Lett. 2009; 11: 2820
- 23 Matsuura BS, Condie AG, Buff RC, Karahalis GJ, Stephenson CR. J. Org. Lett. 2011; 13: 6320
- 24a Wang J, Soisson SM, Young K, Shoop W, Kodali S, Galgoci A, Painter R, Parthasarathy G, Tang YS, Cummings R, Ha S, Dorso K, Motyl M, Jayasuriya H, Ondeyka J, Herath K, Zhang C, Hernandez L, Alloco J, Basilio A, Tormo JR, Genilloud O, Vicente F, Pelaez F, Colwell L, Lee SH, Michael B, Felcetto T, Gill C, Silver LL, Hermes JD, Bartizal K, Barret J, Schmatz D, Becker JW, Cully D, Singh SB. Nature 2006; 441: 358
- 24b Saleem M, Hussain H, Ahmed I, van Ree T, Krohn K. Nat. Prod. Rep. 2011; 28: 1534
-
25a Hegedus LS, Allen GF, Waterman EL. J. Am. Chem. Soc. 1976; 98: 2674
- 25b Hayashi T, Hegedus LS. J. Am. Chem. Soc. 1977; 99: 7093
-
25c Hegedus LS, Allen GF, Bozell JJ, Waterman EL. J. Am. Chem. Soc. 1978; 100: 5800
-
25d Semmelhack MF, Bodurow C. J. Am. Chem. Soc. 1984; 106: 1496
-
25e Semmelhack MF, Zhang N. J. Org. Chem. 1989; 54: 4483
-
25f Semmelhack MF, Epa WR. Tetrahedron Lett. 1993; 34: 7205
- 25g Wolfe JP, Rossi MA. J. Am. Chem. Soc. 2004; 126: 1620
- 25h Lira R, Wolfe JP. J. Am. Chem. Soc. 2004; 126: 13906
- 25i Leathen ML, Rosen BR, Wolfe JP. J. Org. Chem. 2009; 74: 5107
- 25j Rosen BR, Ney JE, Wolfe JP. J. Org. Chem. 2010; 75: 2756
- 25k Bloome KS, Alexanian EJ. J. Am. Chem. Soc. 2010; 132: 12823
- 26 Pouységu L, Sylla T, Garnier T, Rojas LB, Charris J, Deffieux D, Quideau S. Tetrahedron 2010; 66: 5908
- 27 Carman RM, Lambert LK, Robinson WT, Van Dongen JM. A. M. Aust. J. Chem. 1986; 39: 1843
- 28 Hoarau C, Pettus TR. R. Org. Lett. 2006; 8: 2843
- 29 Mejorado LH, Hoarau C, Pettus TR. R. Org. Lett. 2004; 6: 1535
- 30 Vo NT, Pace RD. M, O’Hara F, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 404
- 31 Gu Q, You S. Chem. Sci. 2011; 2: 1519
- 32a Popelak A, Haack E, Lettenbauer G, Spingler H. Naturwissenschaften 1960; 47: 156
- 32b Smith E, Hosansky N, Shamma M, Moss JB. Chem. Ind. 1961; 402
- 33 Gu Q, You S. Org. Lett. 2011; 13: 5192
-
34 Nemoto T, Ishige Y, Yoshida M, Kohno Y, Kanematsu M, Hamada Y. Org. Lett. 2010; 12: 5020
- 35 Liang H, Ciufolini MA. Angew. Chem. Int. Ed. 2011; 50: 11849
- 36 Dohi T, Maruyama A, Takenaga N, Senami K, Minamitsuji Y, Fujioka H, Caemmerer SB, Kita Y. Angew. Chem. Int. Ed. 2008; 47: 3787
- 37a Lewis N, Wallbank P. Synthesis 1987; 1103
- 37b Barret R, Daudon M. Tetrahedron Lett. 1990; 31: 4871
- 37c Mal D, Roy HN, Hazra NK, Adhikari S. Tetrahedron 1997; 53: 2177
- 37d Quideau S, Pouységu L, Oxoby M, Looney MA. Tetrahedron 2001; 57: 319
- 37e Wood JL, Graeber JK, Njardarson JT. Tetrahedron 2003; 59: 8855
- 38a Pelter A, Elgendy S. Tetrahedron Lett. 1988; 29: 677
- 38b Kürti L, Herczegh P, Visy J, Simonyi M, Antus S, Pelter A. J. Chem. Soc., Perkin Trans. 1 1999; 379
- 38c Pelter A, Ward RS. Tetrahedron 2001; 57: 273
- 39a Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
- 39b Uyanik M, Yasui T, Ishihara K. Tetrahedron 2010; 66: 5841
- 40 Quideau S, Lyvinec G, Marguerit M, Bathany K, Ozanne-Beaudenon A, Buffeteau T, Cavagnat D, Chénedé A. Angew. Chem. Int. Ed. 2009; 48: 4605
- 41 Boppisetti JK, Birman VB. Org. Lett. 2009; 11: 1221
- 42 Li F, Tartakoff SS, Castle SL. J. Am. Chem. Soc. 2009; 131: 6674
- 43a Mendelsohn BA, Lee S, Kim S, Teyssier F, Aulakh VS, Ciufolini MA. Org. Lett. 2009; 11: 1539
- 43b Mendelsohn BA, Ciufolini MA. Org. Lett. 2009; 11: 4736
- 44 Frie JL, Jeffrey CS, Sorensen EJ. Org. Lett. 2009; 11: 5394
- 45 For a review covering the oxidation of oximes to nitrile oxides with hypervalent iodine reagents, see: Turner CD, Ciufolini MA. ARKIVOC 2011; (i): 410
- 46 Mejorado LH, Pettus TR. R. J. Am. Chem. Soc. 2006; 128: 15625
- 47 Green JC, Pettus TR. R. J. Am. Chem. Soc. 2011; 133: 1603
- 48 Krawczuk PJ, Schne N, Baran PS. Org. Lett. 2009; 11: 4774
- 49 Mehta G, Maity P. Tetrahedron Lett. 2007; 48: 8865
- 50a Zhu J, Grigoriadis NP, Lee JP, Porco JA. Jr. J. Am. Chem. Soc. 2005; 127: 9342
- 50b Zhu J, Porco JA. Jr. Org. Lett. 2006; 8: 5169
- 51 Dong S, Hamel E, Bai R, Covell GD, Beutler JA, Porco Jr JA. Angew. Chem. Int. Ed. 2009; 48: 1494
- 52 Hu Y, Li C, Kulkarni BA, Strobel G, Lobkovsky E, Torczynski RM, Porco JA. Jr. Org. Lett. 2001; 3: 1649
- 53 Dohi T, Minamitsuji Y, Maruyama A, Hirose S, Kita Y. Org. Lett. 2008; 10: 3559
- 54 Nicolaou KC, Edmonds DJ, Li A, Tria GS. Angew. Chem. Int. Ed. 2007; 46: 3942
- 55 Sabot C, Guérard KC, Canesi S. Chem. Commun. 2009; 2941
- 56 Dai M, Danishefsky SJ. Tetrahedron Lett. 2008; 49: 6610
- 57 Wang X, Porco JA. Jr. Angew. Chem. Int. Ed. 2005; 44: 3067
- 58a Baxendale IR, Ley SV, Piutti C. Angew. Chem. Int. Ed. 2002; 41: 2194
- 58b Baxendale IR, Ley SV, Nessi M, Piutti C. Tetrahedron 2002; 58: 6285
- 59 Baxendale IR, Ley SV. Ind. Eng. Chem. Res. 2005; 44: 8588
- 60 Heckrodt TJ, Mulzer J. J. Am. Chem. Soc. 2003; 125: 4680
- 61 Burgett AW. G, Li Q, Wei Q, Harran PG. Angew. Chem. Int. Ed. 2003; 42: 4961
- 62a Yasui Y, Suzuki K, Matsumoto T. Synlett 2004; 619
- 62b Yasui Y, Koga Y, Suzuki K, Matsumoto T. Synlett 2004; 615
- 63 Onoda T, Takikawa Y, Fujimoto T, Yasui Y, Suzuki K, Matsumoto T. Synlett 2009; 1041
- 64 Ciufolini MA, Braun NA, Canesi S, Ousmer M, Chang J, Chai D. Synthesis 2007; 3759
- 65 Ousmer M, Braun NA, Ciufolini MA. Org. Lett. 2001; 3: 765
- 66a Ciufolini MA, Canesi S, Ousmer M, Braun NA. Tetrahedron 2006; 62: 5318
- 66b Ousmer M, Braun NA, Bavoux C, Perrin M, Ciufolini MA. J. Am. Chem. Soc. 2001; 123: 7534
- 67 Canesi S, Bouchu D, Ciufolini MA. Angew. Chem. Int. Ed. 2004; 43: 4336
- 68 Scheffler G, Seike H, Sorensen EJ. Angew. Chem. Int. Ed. 2000; 39: 4593
- 69 Mizutani H, Takayama J, Soeda Y, Honda T. Tetrahedron Lett. 2002; 43: 2411
Reactions of alkenyliodonium salts with nucleophiles: