Chemical Communications. Electronic Supporting Information
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- Ἕκτωρ Ηλιόπουλος
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1 Chemical Communications Electronic Supporting Information Access to unusual polycyclic spiro enones from 2,2 -bis(allyloxy)-1,1 -binaphthyls using Grubbs catalysts: An unprecedented one-pot RCM/Claisen sequence Estefanía Piedra, Javier Francos, Noel Nebra, Francisco J. Suárez, Josefina Díez, and Victorio Cadierno* Departamento de Química rgánica e Inorgánica, Instituto Universitario de Química rganometálica Enrique Moles (Unidad Asociada al CSIC), Universidad de viedo, Julián Clavería 8, E viedo, Principado de Asturias, Spain. Fax: ; Tel: ; vcm@uniovi.es. - S1 -
2 General methods: All reagents were obtained from commercial suppliers and used without further purification with the exception of compounds 2,2 -bis(allyloxy)-1,1 binaphthyl (1a), 1 6,6 -dibromo-2,2 -dihydroxy-1,1 binaphthyl, 2 7,7 -dibromo-2,2 -dihydroxy-1,1 -binaphthyl, 3 and 7,7 -dimethoxy-2,2 -dihydroxy-1,1 -binaphthyl, 4 which were prepared by following the methods reported in the literature. Flash chromatography was performed using Merck silica gel 60 ( mesh). Infrared spectra were recorded on a Perkin-Elmer 1720-XFT spectrometer. NMR spectra were recorded on a uker DPX-300 instrument at 300 MHz ( 1 H) or 75.4 MHz ( 13 C). The chemical shift values (δ) are given in parts per million and are referred to the residual peak of the deuterated solvent used (CDCl 3 ). ESI- TF high-resolution mass spectra were provided by the mass spectrometry service of the University of Seville (Spain). Preparation of 2,2 -bis(allyloxy)-6,6 -dibromo-1,1 binaphthyl (1b): A solution of 6,6 -dibromo-2,2 -dihydroxy- 1,1 -binaphthyl (4.44 g, 10 mmol) in 60 ml of dry acetone was treated, under nitrogen atmosphere, with KH (1.68 g, 30 mmol) at 60 ºC for 1 hour. Allyl bromide (2.2 ml, 25 mmol) was then added and the resulting solution heated at 60 ºC for additional 24 hours. The mixture was cooled to room temperature, filtered, and the filtrate concentrated under reduced pressure to give a pale yellow solid. The crude product was purified by flash chromatography (silica gel; eluent AcEt/hexane 1:20) to afford 1b as a white solid (0.40 g, 84%). IR (Nujol) ν 1580 (C=C) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 4.55 (m, 4H), 5.05 (m, 4H), 5.76 (m, 2H), 7.01 (d, J = 9.0 Hz, 2H), 7.30 (dd, J = 9.0 and 2.0 Hz, 2H), 7.42 (d, J = 9.0 Hz, 2H), 7.87 (d, J = 9.0 Hz, 2H), 8.04 (d, J = 2.0 Hz, 2H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 70.2, 116.8, 117.1, 117.9, 120.2, 127.5, 128.9, - S2 -
3 130.0, 130.3, 130.7, 132.9, 133.7, ppm; HRMS (ESI- TF) m/e (M + ) (C 26 H requires ). Preparation of 2,2 -bis(allyloxy)-7,7 -dibromo-1,1 binaphthyl (1c): Compound 1c, isolated as a white solid in 81% yield (4.25 g), was prepared as described for 1b starting from 7,7 -dibromo-2,2 -dihydroxy-1,1 -binaphthyl (4.44 g, 10 mmol) and allyl bromide (2.2 ml, 25 mmol). IR (Nujol) ν 1615 (C=C) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 4.58 (br, 4H), 5.06 (m, 4H), 5.77 (m, 2H), (m, 6H), 7.75 (d, J = 8.7 Hz, 2H), 8.93 (d, J = 9.0 Hz, 2H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 69.7, 115.6, 116.9, 118.7, 121.1, 127.1, 127.2, 127.7, 129.6, 129.7, 133.3, 135.3, ppm; HRMS (ESI-TF) m/e (M + ) (C 26 H requires ). Preparation of 2,2 -bis(allyloxy)-7,7 -dimethoxy-1,1 binaphthyl (1d): Compound 1d, isolated as a white solid in 74% yield (3.15 g), was prepared as described for 1b starting from 7,7 -dimethoxy-2,2 -dihydroxy-1,1 -binaphthyl (4.26 g, 10 mmol) and allyl bromide (2.2 ml, 25 mmol). IR (Nujol) ν 1614 (C=C) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 3.60 (s, 6H), 4.64 (br, 4H), 5.15 (m, 4H), 5.89 (m, 2H), 6.74 (s, 2H), 7.16 (d, J = 8.8 Hz, 2H), 7.36 (d, J = 8.9 Hz, 2H), 7.86 (d, J = 8.8 Hz, 2H), 7.95 (d, J = 8.9 Hz, 2H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 55.0, 69.8, 104.2, 113.0, 116.3, 116.5, 119.6, 125.1, 129.1, 129.7, 134.0, 135.6, 154.8, ppm; HRMS (ESI-TF) m/e (M + ) (C 28 H 26 4 requires ). General procedure for the catalytic reactions: Under nitrogen atmosphere, the corresponding 2,2 -bis(allyloxy)- 1,1 -binaphthyl derivative 1a-d (0.5 mmol), the ruthenium catalyst [RuCl 2 (=CHPh)(PCy 3 ) 2 ] (0.012 g, mmol; 3 mol% - S3 -
4 of Ru) and dichloromethane (10 ml) were introduced into a crimp-sealed thick-walled glass tube equipped with a pressure sensor and a magnetic stirrer. The tube was then placed inside the cavity of a CEM Discover S-Class microwave synthesizer and exposed to MW-irradiation at a constant temperature of 120 ºC (temperature monitored by a built-in infrared sensor) for 3 hours (MW power 300 W; P max psi). After removal of volatiles under vacuum, the solid residue was purified by column chromatography over silica gel. Thus, initial elution with EtAc/hexanes (1:10) gave a colourless band from which spriro enones 2a-d were obtained by solvent removal. Further elution with EtAc/hexanes (1:5) gave a second band from which macrocycles 3a-b could be isolated in pure form. Characterization data for all these new compounds are as follows: 2-vinyl-2,3-dihydro-2'H-spiro[benzo[f]chromene-1,1'- naphthalen]-2'-one (2a): White solid; Yield: g (79%); IR (Nujol) ν 1617 (C=C), 1660 (C=) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 2.99 (m, 1H), 4.12 (dd, J = 11.1 and 3.4 Hz, 1H), 4.56 (t, J = 10.8 Hz, 1H), 4.66 (d, J = 17.0 Hz, 1H), 4.93 (d, J = 10.5 Hz, 1H), 5.50 (m, 1H), 6.38 (d, J = 9.5 Hz, 1H), 6.65 (d, J = 8.5 Hz, 1H), 6.80 (d, J = 8.5 Hz, 1H), (m, 5H), 7.42 (d, J = 8.5 Hz, 1H), 7.67 (m, 3H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 54.4, 56.9, 63.0, 115.7, 118.5, 119.0, 123.0, 123.8, 126.3, 126.9, 127.5, 128.5, 129.1, 129.9, 13021, 130.3, 130.7, 131.1, 131.6, 145.5, 147.6, 154.9, ppm; HRMS (ESI-TF) m/e (M + + H) (C 24 H 19 2 requires ). - S4 -
5 7,8-dibromo-2-vinyl-2,3-dihydro-2'Hspiro[benzo[f]chromene-1,1'-naphthalen]-2'-one (2b): White solid; Yield: g (73%); IR (Nujol) ν 1616 (C=C), 1655 (C=) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 2.94 (m, 1H), 4.12 (dd, J = 10.5 and 2.6 Hz, 1H), 4.54 (t, J = 10.6 Hz, 1H), 4.72 (d, J = 17.2 Hz, 1H), 4.99 (d, J = 10.3 Hz, 1H), 5.49 (m, 1H), 6.40 (d, J = 9.9 Hz, 1H), 6.48 (d, J = 9.2 Hz, 1H), 6.64 (d, J = 8.3 Hz, 1H), (m, 3H), (m, 3H), 7.86 (br, 1H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 56.4, 58.7, 64.9, 117.4, 118.8, 121.2, 122.3, 122.8, 127.3, 129.4, 131.2, 131.7, 132.1, 132.5, 132.6, 133.5, 133.6, 134.2, 135.5, 145.9, 148.0, 157.3, ppm; HRMS (ESI-TF) m/e (M + + H) (C 24 H requires ). 6,9-dibromo-2-vinyl-2,3-dihydro-2'Hspiro[benzo[f]chromene-1,1'-naphthalen]-2'-one (2c): White solid; Yield: g (67%); IR (Nujol) ν 1615 (C=C), 1651 (C=) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 3.00 (m, 1H), 4.14 (dd, J = 11.2 and 3.7 Hz, 1H), 4.57 (t, J = 10.9 Hz, 1H), 4.74 (d, J = 17.0 Hz, 1H), 4.98 (d, J = 10.4 Hz, 1H), 5.47 (m, 1H), 6.44 (d, J = 9.9 Hz, 1H), 6.84 (d, J = 1.3 Hz, 1H), 6.94 (d, J = 1.8 Hz, 1H), (m, 7H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 54.5, 56.4, 63.0, 114.5, 119.3, 119.7, 121.1, 125.7, 125.9, 126.6, 126.7, 128.7, 129.4, 130.1, 130.3, 130.4, 130.5, 130.8, 132.8, 144.4, 149.0, 155.7, ppm; HRMS (ESI-TF) m/e (M + + H) (C 24 H requires ). - S5 -
6 6,9-dimethoxy-2-vinyl-2,3-dihydro-2'Hspiro[benzo[f]chromene-1,1'-naphthalen]-2'-one (2d): White solid; Yield: g (70%); IR (Nujol) ν 1621 (C=C), 1656 (C=) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 3.06 (m, 1H), 3.34 (s, 3H), 3.61 (s, 3H), 4.12 (dd, J = 11.0 and 3.7 Hz, 1H), 4.62 (t, J = 11.2 Hz, 1H), 4.75 (d, J = 17.0 Hz, 1H), 4.98 (d, J = 10.4 Hz, 1H), 5.55 (m, 1H), 6.02 (d, J = 2.4 Hz, 1H), 6.32 (d, J = 9.9 Hz, 1H), 6.39 (d, J = 2.6 Hz, 1H), 6.78 (d, J = 2.4 Hz, 1H), 6.81 (d, J = 2.6 Hz, 1H), 7.07 (d, J = 9.0 Hz, 1H), 7.36 (d, J = 8.4 Hz, 1H), (m, 3H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 54.6, 54.7, 55.2, 56.9, 63.1, 103.1, 112.3, 113.9, 115.3, 115.9, 116.4, 118.6, 124.2, 124.5, 125.4, 129.5, 129.9, 130.3, 130.9, 132.9, 144.8, 150.2, 155.5, 157.9, 162.0, ppm; HRMS (ESI-TF) m/e (M + + H) (C 26 H 23 4 requires ). (13E,31E)-12,15,30,33-tetrahydrotetranaphtho[2,1-b:1',2'- d:2'',1''-l:1''',2'''][1,6,11,16]tetraoxacycloicosine (3a): White solid; Yield: g (8%); IR (Nujol) ν 1591 (C=C) cm -1 ; 1 H NMR (CDCl 3, 300 MHz) δ 4.44 (m, 8H), 5.59 (br, 4H), (m 16H), 7.82 (d, J = 8.9 Hz, 4H), 7.94 (d, J = 8.3 Hz, 4H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 70.4, 116.8, 121.8, 125.4, 127.4, 128.2, 129.9, 131.1, 136.1, ppm; HRMS (ESI-TF) m/e (M + ) (C 48 H 36 4 requires ). (13E,31E)-2,7,20,25-tetrabromo-12,15,30,33- tetrahydrotetranaphtho[2,1-b:1',2'-d:2'',1''-l:1''',2'''- n][1,6,11,16]tetraoxacycloicosine (3b): White solid; Yield: g (9%); IR (Nujol) ν 1585 (C=C) cm -1 ; 1 H NMR (CDCl 3, - S6 -
7 300 MHz) δ 4.43 (m, 8H), 5.67 (br, 4H), 6.90 (d, J = 9.0 Hz, 4H), 7.13 (d, J = 9.0 Hz, 4H), 7.30 (m, 4H), 7.68 (d, J = 9.0 Hz, 4H), 8.08 (s, J = 1.7 Hz, 4H) ppm; 13 C{ 1 H} NMR (CDCl 3, 75.4 MHz) δ 70.0, 117.3, 119.3, 121.1, 129.0, 129.6, 130.3, 131.6, 131.8, 132.0, 134.4, ppm; HRMS (ESI-TF) m/e (M + ) (C 48 H requires ). Theoretical Calculations: The theoretical calculations were performed using the program package Gaussian03, 5 at density functional theory (DFT) level by means of the hybrid B3LYP functional. 6 In all geometry optimizations, Pople's 6-31G(d) split valence basis set was used for C, H and elements. Frequency calculations were performed to determine whether the optimized geometries were minima on the potential energy surface. ptimized geometries of (SS)- 3a and (RS)-3a are shown in Figures S1 and S2, respectively. Figure S1. ptimized structure of (SS)-3a. - S7 -
8 Figure S2. ptimized structure of (RS)-3a. Cartesian coordinates and total electronic energies (Hartree) for the computed species (SS)-3a and (RS)-3a: (SS)-3a: E(gas) : C C C C C C C C C C C C C C C C S8 -
9 C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C H H S9 -
10 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S10 -
11 (RS)-3a: E (gas) = C C C C C C C C C C C C C C C C C C C C C C C C C C C S11 -
12 C C C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H S12 -
13 H H H H H H H H H H H H H H H H H H H H H H H References: 1 H.-T. Stock and R. M. Kellogg, J. rg. Chem., 1996, 61, K. Ding, Y. Wang, L. Zhang, Y. Wu and T. Matsuura, Tetrahedron, 1996, 52, S13 -
14 3 M. Bandin, S. Casolari, P. G. Cozzi, G. Proni, E. Schmohel, G. P. Spada, E. Tagliavini and A. Umani- Ronchi, Eur. J. rg. Chem., 2000, J. K. Joseph, S. L. Jain and B. Sain, Catal. Commun., 2006, 7, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda,. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann,. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. chterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain,. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. rtiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al- Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, in Gaussian 03, Revision C.02: Gaussian, Inc., Wallingford CT, (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648; (b) C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785; (c) P. J. Stephens, F. J. Devlin, C. F. Chabalowski and M. J. Frisch, J. Phys. Chem., 1994, 98, S14 -
15 Figure S3. The twisted conformation adopted by the 1,1 - binaphthyl-2,2 -diyl unit in intermediate A. - S15 -
16 Copies of the compounds: 1 H and 13 C{ 1 H} NMR spectra of all new (1b) (1b) - S16 -
17 (1c) (1c) - S17 -
18 Me Me (1d) Me Me (1d) - S18 -
19 (2a) (2a) - S19 -
20 (2b) (2b) - S20 -
21 (2c) (2c) - S21 -
22 Me Me (2d) Me Me (2d) - S22 -
23 (3a) (3a) - S23 -
24 Electronic Supplementary Material (ESI) for Chemical Communications (3b) (3b) - S24 -
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