Tianhua SHEN, Quan QIN, Hang NI, Ting XIA, Xiaocong ZHOU, Funa CUI, Junqi LI, Deqiang RAN, Qingbao SONG

Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

The Cu(I)-based complex prepared from (S)-2-(furan-2-yl-methylamino)-2-phenylethanol (5c) and CuCl was used as catalyst in enantioselective Henry reactions of arylaldehydes and nitromethane, which gave 89% ee and 95% yield at ambient temperature. The proposed catalytic cycle of an asymmetric Henry reaction was suggested.

Anahtar Kelimeler:

Chiral amino alcohol, copper(I) salt, asymmetric catalysis, Henry reaction

Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

Keywords:

Chiral amino alcohol, copper(I) salt, asymmetric catalysis, Henry reaction,

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Henry, L. C. R. Hebd. Seances Acad. Sci. 1895, 120, 1265. a) Coppola, G. M.; Schuster, H. F. α -Hydroxy Acids in Enantioselective Syntheses, VCH, Weinheim, 1997. b) Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017–1047. c) Narayana, C.; Reddy, N. K.; Kabalka, G. W. Synth. Commun. 1992, 22, 2587–2592. d) Matt, C.; Wagner, A.; Mioskowski, C. J. Org. Chem. 1997, 62, 234–235. e) Bergmeier, S. C. Tetrahedron 2000, 56, 2561–2576. f) Poupart, M.-A.; Fazal, G.; Goulet, S.; Mar, L. T. J. Org. Chem. 1999, 64, 1356–1361. a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418–4420; b) Sasai, H.; Tokunaga, T.; Watenabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388–7389.
For a review see: Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561–2574. a) Christensen, C.; Juhl, K.; Jİrgensen, K. A. Chem. Commun. 2001, 2222–2223; b) Christensen, C.; Juhl, K.; Hazell, R. G.; Jİrgensen, K. A. J. Org. Chem. 2002, 67, 4875–4881. c) Lu, S.-F.; Du, D.-M.; Zhang, S.-W.; Xu, J. Tetrahedron: Asymmetry 2004, 15, 3433–3441; d) Du, D.-M.; Lu, S.-F.; Fang, T.; Xu, J. J. Org. Chem. 2005, 70, 3712–3715. e) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T. Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692–12693. f) Gaab, M.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Eur. J. 2009, 15, 5450–5462. Toussaint, A.; Pfaltz, A. Eur. J. Org. Chem. 2008, 4591–4597.
Spangler, K. Y.; Wolf, C. Org. Lett. 2009, 11, 4724–4727. a) Mansawat, W.; Saengswang. I.; U-prasitwong, P.; Bhanthumnavin, W.; Vilaivan, T. Tetrahedron Lett. 2007, 48, 4235–4238. b) Kim, H. U.; Oh, K. Org. Lett. 2009, 11, 5682–5685. a) Gan, C.; Lai, G.; Zhang, Z.; Wang, Z.; Zhou, M.-M. Tetrahedron: Asymmetry 2006, 17, 725–728. b) Jammi, S.; Punniyamurthy, T. Eur. J. Inorg. Chem. 2009, 2508–2511. c) Guo, J.; Mao, J. Chirality 2009, 21, 619–627.
Blay, G.; Domingo, L. R.; Hern´ andez-Olmos, V.; Pedro, J. R. Chem. Eur. J. 2008, 14, 4725–4730. a) Blay, G.; Climent, E.; Fern´ andez, I.; Hern´ andez-Olmos, V.; Pedro, J. R. Tetrahedron: Asymmetry 2006, 17, 2046–2049. b) Blay, G.; Climent, E.; Fern´ andez, I.; Hern´ andez-Olmos, V.; Pedro, J. R. Tetrahedron: Asymmetry 2007, 18, 1603–1612. c) Blay, G.; Hern´ andez-Olmos, V.; Pedro, J. R. Org. Biomol. Chem. 2008, 6, 468–476.
Noole, A.; Lippur, K.; Metsala, A.; Lopp, M.; Kanger, T. J. Org. Chem. 2010, 75, 1313–1316.
Bureˇ sa, F.; Kulh´ anek, J.; R˚ uˇ ziˇ cka, A. Tetrahedron Lett. 2009, 50, 3042–3045.
Bureˇ s, F.; Szotkowski, T.; Kulh´ anek, J.; Pytela, O.; Ludwiga, M.; Holˇ capek, M. Tetrahedron: Asymmetry 2006, 17, 900–907.
Maheswaran, H.; Prasanth, K. L.; Krishna, G. G.; Ravikumar, K.; Sridhar, B.; Kantam, M. L. Chem. Commun. 2006, 4066–4068.
Breuning, M.; Hein, D.; Steiner, M.; Gessner, V. H.; Strohmann, C. Chem. Eur. J. 2009, 15, 12764–12769. a) Arai, T.; Watanabe, M.; Fujiwara, A.; Yokoyama, N.; Yanagisawa, A. Angew. Chem. Int. Ed. 2006, 45, 5978– 59 b) Bandini, M.; Benaglia, M.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. Org. Lett. 2007, 9, 2151–2153. c) Bandini, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A.; Ventrici, C. Chem. Commun. 2007, 616–618. d) Kowalczyk, R.; Sidorowicz, L.; Skar˙zewski, J. Tetrahedron: Asymmetry 2008, 19, 2310–2315. e) Arai, T.; Takashita, R.; Endo, Y.; Watanabe, M.; Yanagisawa, A. J. Org. Chem. 2008, 73, 4903–4906. f) Kowalczyk, R.; Skar˙zewski, J. Tetrahedron: Asymmetry 2009, 20, 2467–2473. g) Selvakumar, S.; Sivasankarana, D.; Singh, V. K. Org. Biomol. Chem. 2009, 7, 3156–3162. h) Zhang, G.; Yashima, E.; Woggona, W. D. Adv. Synth. Catal. 2009, 351, 1255–1262. Tanaka, K.; Hachiken, S.; Tetrahedron Lett. 2008, 49, 2533–2536.
Jammi, S.; Saha, P.; Sanyashi, S.; Sakthivel, S.; Punniyamurthy, T. Tetrahedron 2008, 64, 11724–11731.
Qin, B.; Xiao, X.; Liu, X.; Huang, J.; Wen, Y.; Feng, X. J. Org. Chem. 2007, 72, 9323–9328. a) Xiong, Y.; Wang, Fei.; Huang, X.; Wen, Y.; Feng, X. Chem. Eur. J. 2007, 13, 829–833. b) Constable, E. C.; Zhang, G.; Housecroft, C. E.; Neuburger, M.; Schaffner, S.; Woggon, W. D.; Zampese, J. A. New J. Chem. 2009, 33, 2166–2173.
Zieli´ nska-Blajet, M.; Skar˙zewski, J. Tetrahedron: Asymmetry 2009, 20, 1992–1998.
Bandini, M.; Cabiddu, S.; Cadoni, E.; Olivelli, P.; Sinisi, R.; Umani-Ronchi, A.; Usai, M. Chirality 2009, 21, 239–244.
Cristiane, F. D. C.; Alessandra, C. P. Chem. Biol. Drug. Des. 2012, 79, 216-222.
Da, C.; Han, Z.; Ni, M.; Yang, F.; Liu, D.; Zhou, Y.; Wang, R. Tetrahedron: Asymmetry 2003, 14, 659–665.
Giannis, A.; Sandhoff, K. Angew. Chem. Int. Ed. Engl. 1989, 28, 218–219.
Carrillo, L.; Bad´ıa, D.; Dom´ınguez, E.; Ortega, F.; Tellitu, I. Tetrahedron Asymmetry 1998, 9, 151–155.
Benningshof, J. C. R.; Blaauw, R. H.; Ginkel, A. E.; Maarseveen, J. H.; Rutjes, F. P. J. T.; Hiemstra, H. J. Chem. Soc. Perkin Trans. I 2002, 1693–1700.
Alvaro, G.; Fabio, R. D.; Gualandi, A.; Savoia, D. Eur. J. Org. Chem. 2007, 5573–5582.
Hiroshi, K.; Mikio, S.; Yoshio, O. PCT. Int. Appl. 9417079, 1994.