Synthesis 2016; 48(12): 1927-1933
DOI: 10.1055/s-0035-1561604
special topic
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed Dimeric Cyclization of Isoeugenol and Related 1-Phenylpropenes in Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of 1,2,3-Trisubstituted 2,3-Dihydro-1H-indenes

Nobuyoshi Morita*
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Rie Mashiko
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Dai Hakuta
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Daisuke Eguchi
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Shintaro Ban
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Yoshimitsu Hashimoto
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Iwao Okamoto
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
,
Osamu Tamura*
Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan   eMail: morita@ac.shoyaku.ac.jp   eMail: tamura@ac.shoyaku.ac.jp
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Publikationsverlauf

Received: 30. Januar 2016

Accepted after revision: 09. März 2016

Publikationsdatum:
20. April 2016 (online)

Abstract

Gold-catalyzed dimerization of isoeugenol and related 1-phenylpropenes in ionic liquid enabled environmentally friendly, stereo­selective synthesis of 1,2,3-trisubstituted 2,3-dihydro-1H-indenes. Dimerization of isoeugenol or isohomogenol afforded diisoeugenol or diisohomogenol, respectively, with α-configuration, whereas dimerization of α-asarone furnished diasarone with γ-configuration.

Supporting Information

 
  • References


    • For reviews on lignans and neolignans, see:
    • 1a Saleem M, Kim HJ, Ali MS, Lee YS. Nat. Prod. Rep. 2005; 22: 696
    • 1b MacRae WD, Towers GH. N. Phytochemistry 1984; 23: 1207
    • 1c Ward RS. Chem. Soc. Rev. 1982; 11: 75

      In earliest researches, 2,3-dihydro-1H-indene derivatives were originally thought to be derivatives of cyclobutane or 9,10-dihydroanthracene. The skeletons of 2,3-dihydro-1H-indenes were first proposed by Baker et al. in 1940, and MacMillan et al. assigned the correct stereochemical structure for the dimers derived from (E)-isosafrole and isohomogenol in 1969:
    • 2a Baker W, Enderby J. J. Chem. Soc. 1940; 1094
    • 2b MacMillan J, Martin IL, Morris DJ. Tetrahedron 1969; 25: 905
  • 3 Puxeddu E. Gazz. Chim. Ital. 1909; 39: 131
    • 4a Saxena DB. Phytochemistry 1986; 25: 553
    • 4b Bohlmann F, Gracza L. Arch. Pharm. (Weinheim) 1982; 315: 474
    • 5a Atsumi T, Tonosaki K, Fujisawa S. Arch. Oral Biol. 2006; 51: 913
    • 5b Atsumi T, Murakami Y, Shibuya K, Tonosaki K, Fujisawa S. Anticancer Res. 2005; 25: 4029
  • 6 Murakami Y, Shoji M, Hirata A, Tanaka S, Yokoe I, Fujisawa S. Arch. Biochem. Biophys. 2005; 434: 326
  • 7 Ko F.-N, Liao C.-H, Kuo Y.-H, Lin Y.-L. Biochim. Biophys. Acta 1995; 1258: 145
  • 8 Lin C.-H, Kuo Y.-H, Lin Y.-L, Teng C.-M. J. Pharm. Pharmacol. 1994; 46: 54
  • 9 Danilova LI, Ivanova IYa, Kozlova ZG, Kore SA, Livshits AG, Osipova VP, Tsepalov VF, Shlyapintokh VYa. Patent SU No. 224741, 1968

    • For dimerization with catalysts, see:
    • 10a Kouznetsov VV, Merchan Arenas DR. Tetrahedron Lett. 2009; 50: 1546
    • 10b Gonzalez-de-Castro A, Xiao J. J. Am. Chem. Soc. 2015; 137: 8206

      For dimerization with Brønsted acid, see:
    • 11a Davis MC, Guenthner AJ, Groshens TJ, Reams JT, Mabry JM. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 4127
    • 11b Alvarez-Thon L, Carrasco-Altamirano H, Espinoza-Catálan L, Gallardo-Araya C, Cardona-Villada W, Ibañez A. Acta Crystallogr. 2006; E62: o2000
    • 11c Al-Farhan E, Keehn PM, Stevenson R. J. Chem. Res., Synop. 1992; 100
    • 11d Al-Farhan E, Keehn PM, Stevenson R. J. Chem. Res., Synop. 1992; 36

      For dimerization with silica-supported acids or solid acids, see:
    • 12a Alesso E, Torviso R, Erlich M, Finkielsztein L, Lantaño B, Moltrasio G, Aguirre J, Vázquez P, Pizzio L, Cáceres C, Blanco M, Thomas H. Synth. Commun. 2002; 32: 3803
    • 12b Alesso EN, Aguirre J, Lantaño B, Finkielsztein L, Moltrasio GY, Vázquez PG, Pizzio LR, Caceres C, White M, Thomas HJ. Molecules 2000; 5: 414

    • For other examples, see:
    • 12c Grigor’eva NG, Talipova RR, Korzhova LF, Vosmerikov AV, Kutepov BI, Dzheimilev UM. Russ. Chem. Bull. 2009; 58: 59
    • 12d Madhavan D, Murugalakshmi M, Lalitha A, Pitchumani K. Catal. Lett. 2001; 73: 1
    • 12e Benito A, Corma A, García H, Primo J. Appl. Catal., A 1994; 116: 127
  • 13 For intramolecular coupling reaction of 1-phenylpropan-1-ols with 1-phenylpropenes, see: Sarnpitak P, Trongchit K, Kostenko Y, Sathalalai S, Gleeson MP, Ruchirawat S, Ploypradith P. J. Org. Chem. 2013; 78: 8281

    • For intermolecular coupling reaction of 1-phenylpropan-1-ols with 1-phenylpropenes, see:
    • 14a Li H.-H. Chin. Chem. Lett. 2015; 26: 320
    • 14b Lantaño B, Aguirre JM, Ugliarolo EA, Benegas ML, Moltrasio GY. Tetrahedron 2008; 64: 4090
    • 14c Pizzio LR, Vázquez PG, Cáceres CV, Blanco MN, Alesso EN, Torviso MR, Lantaño B, Moltrasio GY, Aguirre JM. Appl. Catal., A 2005; 287: 1
    • 14d Lantaño B, Aguirre JM, Finkielsztein L, Alesso EN, Brunet E, Moltrasio GY. Synth. Commun. 2004; 34: 625
    • 14e Alesso E, Torviso R, Lantaño B, Erlich M, Finkielsztein LM, Moltrasio G, Aguirre JM, Brunet E. ARKIVOC 2003; : 283
    • 14f Angle SR, Arnaiz DO. J. Org. Chem. 1992; 57: 5937

      For gold-catalyzed reactions in ionic liquids, see:
    • 15a Lempke L, Fischer T, Bell J, Kraus W, Rurack K, Krause N. Org. Biomol. Chem. 2015; 13: 3787
    • 15b Cui D.-M, Ke Y.-N, Zhuang D.-W, Wang Q, Zhang C. Tetrahedron Lett. 2010; 51: 980
    • 15c Neaţu F, Pârvulescu VI, Michelet V, Gênet J.-P, Goguet A, Hardacre C. New J. Chem. 2009; 33: 102
    • 15d Aksin Ö, Krause N. Adv. Synth. Catal. 2008; 350: 1106
    • 15e Ambrogio I, Arcadi A, Cacchi S, Fabrizi G, Marinelli F. Synlett 2007; 1775
    • 15f Liu X, Pan Z, Shu X, Duan X, Liang Y. Synlett 2006; 1962
    • 16a Lee JW, Shin JY, Chun YS, Jang HB, Song CE, Lee S.-g. Acc. Chem. Res. 2010; 43: 985
    • 16b Park BY, Ryu KY, Park JH, Lee S.-g. Green Chem. 2009; 11: 946
    • 16c Kim JH, Lee JW, Shin US, Lee JY, Lee S.-g, Song CE. Chem. Commun. 2007; 4683
    • 16d Song CE, Jung D.-u, Choung SY, Roh EJ, Lee S.-g. Angew. Chem. Int. Ed. 2004; 43: 6183
    • 16e Song CE, Shim WH, Roh EJ, Lee S.-g, Choi JH. Chem. Commun. 2001; 1122
    • 16f Song CE, Shim WH, Roh EJ, Choi JH. Chem. Commun. 2000; 1695
    • 17a Clement ND, Cavell KJ. Angew. Chem. Int. Ed. 2004; 43: 3845
    • 17b McGuinness DS, Cavell KJ, Yates BF. Chem. Commun. 2001; 355
    • 17c Mathews CJ, Smith PJ, Welton T, White AJ. P, Williams DJ. Organometallics 2001; 20: 3848
    • 17d Xu L, Weiping C, Xiao J. Organometallics 2000; 19: 1123
    • 17e Herrmann WA, Elison M, Fischer J, Köcher C, Artus GR. J. Angew. Chem., Int. Ed. Engl. 1995; 34: 2371
  • 18 Stereochemical assignments of diisohomogenol (4) and related 1,2,3-trisubstituted 2,3-dihydro-1H-indenes were conducted by MacMillan et al. with 1H NMR spectra and comprehensive double irradiation experiments (see ref. 2b). They had shown chemical shifts (ppm) and coupling constants (J values) for the α-, β-, and γ-configuration for three of the diisohomogenol (4) and related 1,2,3-trisubstituted 2,3-dihydro-1H-indenes. Moreover, Lantaño et al. also showed similar tendency of chemical shifts (ppm) and coupling constants (J values) for α-, β- and γ-configuration for various types of 1,2,3-trisubstituted 2,3-dihydro-1H-indenes with NMR experiments (see Ref. 14b).
    • 19a Yamamoto Y. J. Org. Chem. 2007; 72: 7817
    • 19b De Graaf PW. J, Boersma J, van der Kerk GJ. M. J. Organomet. Chem. 1976; 105: 399