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

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.

Key words

gold-catalyzed dimerization - ionic liquid - addition - cyclization - 1,2,3-trisubstituted 2,3-dihydro-1H-indenes

• 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