Highly enantioselective 1,4-conjugate addition of diethylzinc to acyclic enones with chiral phosphite-pyridine ligands derived from H8-NOBIN

Tetrahedron Asymmetry

Volumn 14, Issue 24, 2003, Pages 3907-3915

  Hu, Yuanchun ^a   Liang, Xinmiao ^a   Wang, Junwei ^a   Zheng, Zhuo ^a   Hu, Xinquan ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 2' HYDROXY 5,5',6,6',7,7',8,8' OCTAHYDRO 1,1' BINAPHTHYL; 2,2' DIHYDROXY 5,5',6,6',7,7',8,8' OCTAHYDRO 1,1' BINAPHTHYL; CHALCONE DERIVATIVE; COPPER; DIETHYLZINC; HYDROXYL GROUP; KETONE DERIVATIVE; LIGAND; NAPHTHYL GROUP; PHOSPHITE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATE; DERIVATIZATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0345170098     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.09.020     Document Type: Article

References (64)

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35. 8-1,1′- binaphthyl, see: (a) Zhang, F.-Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337; (b) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808; (c) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179; (d) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991; (e) Chan, A. S. C; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080; (f) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651; (g) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510; (h) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.
36. 8-1,1′- binaphthyl, see: (a) Zhang, F.-Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337; (b) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808; (c) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179; (d) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991; (e) Chan, A. S. C; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080; (f) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651; (g) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510; (h) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.
37. 8-1,1′- binaphthyl, see: (a) Zhang, F.-Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337; (b) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808; (c) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179; (d) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991; (e) Chan, A. S. C; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080; (f) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651; (g) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510; (h) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.
38. 8-1,1′- binaphthyl, see: (a) Zhang, F.-Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337; (b) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808; (c) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179; (d) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991; (e) Chan, A. S. C; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080; (f) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651; (g) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510; (h) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.
39. 8-1,1′- binaphthyl, see: (a) Zhang, F.-Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337; (b) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808; (c) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179; (d) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991; (e) Chan, A. S. C; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080; (f) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651; (g) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510; (h) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.
40. 8-1,1′- binaphthyl, see: (a) Zhang, F.-Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337; (b) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808; (c) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179; (d) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991; (e) Chan, A. S. C; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080; (f) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651; (g) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510; (h) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.
41. 8-1,1′- binaphthyl, see: (a) Zhang, F.-Y.; Kwok, W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 2337; (b) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808; (c) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1998, 9, 1179; (d) Liu, G.-B.; Tsukinoki, T.; Kanda, T.; Mitoma, Y.; Tashiro, M. Tetrahedron Lett. 1998, 39, 5991; (e) Chan, A. S. C; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080; (f) Zhang, F.-Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651; (g) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510; (h) Zhang, X.; Taketomi, T.; Yoshizumi, T.; Kumobayashi, H.; Akutagawa, S.; Mashima, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 3318.
42. 8-BINOL, see: (a) Guo, R.; Au-Yeung, T. T.-L.; Wu, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 2519; (b) Zeng, Q.; Liu, H.; Mi, A.; Jiang, Y. ; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron 2002, 58, 8799; (c) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175; (d) Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10; (f) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115 and references cited therein.
43. 8-BINOL, see: (a) Guo, R.; Au-Yeung, T. T.-L.; Wu, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 2519; (b) Zeng, Q.; Liu, H.; Mi, A.; Jiang, Y. ; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron 2002, 58, 8799; (c) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175; (d) Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10; (f) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115 and references cited therein.
44. 8-BINOL, see: (a) Guo, R.; Au-Yeung, T. T.-L.; Wu, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 2519; (b) Zeng, Q.; Liu, H.; Mi, A.; Jiang, Y. ; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron 2002, 58, 8799; (c) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175; (d) Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10; (f) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115 and references cited therein.
45. 8-BINOL, see: (a) Guo, R.; Au-Yeung, T. T.-L.; Wu, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 2519; (b) Zeng, Q.; Liu, H.; Mi, A.; Jiang, Y. ; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron 2002, 58, 8799; (c) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175; (d) Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10; (f) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115 and references cited therein.
46. 8-BINOL, see: (a) Guo, R.; Au-Yeung, T. T.-L.; Wu, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 2519; (b) Zeng, Q.; Liu, H.; Mi, A.; Jiang, Y. ; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron 2002, 58, 8799; (c) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175; (d) Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10; (f) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115 and references cited therein.
47. 8-BINOL, see: (a) Guo, R.; Au-Yeung, T. T.-L.; Wu, J.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 2519; (b) Zeng, Q.; Liu, H.; Mi, A.; Jiang, Y. ; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron 2002, 58, 8799; (c) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175; (d) Lu, G.; Li, X.; Chan, W. L.; Chan, A. S. C. Chem. Commun. 2002, 172; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10; (f) Zeng, Q.; Liu, H.; Cui, X.; Mi, A.; Jiang, Y.; Li, X.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2002, 13, 115 and references cited therein.
48. 8-NOBIN, see: (a) Wang, Y.; Li, X.; Sun, J.; Ding. K. Organometallics 2003, 22, 1856; (b) Wang, Y.; Ji, B.; Ding, K. Chin. J. Chem. 2002, 20, 1300; (c) Wang, Y.; Li, X.; Ding, K. Tetrahedron Lett. 2002, 43, 159; (d) Guo, H.; Wang, Y.; Ding K. Chin. J. Chem. 2001, 19, 52; (e) Wang, Y.; Guo, H.; Ding, K. Tetrahedron: Asymmetry 2000, 11, 4153.
49. 8-NOBIN, see: (a) Wang, Y.; Li, X.; Sun, J.; Ding. K. Organometallics 2003, 22, 1856; (b) Wang, Y.; Ji, B.; Ding, K. Chin. J. Chem. 2002, 20, 1300; (c) Wang, Y.; Li, X.; Ding, K. Tetrahedron Lett. 2002, 43, 159; (d) Guo, H.; Wang, Y.; Ding K. Chin. J. Chem. 2001, 19, 52; (e) Wang, Y.; Guo, H.; Ding, K. Tetrahedron: Asymmetry 2000, 11, 4153.
50. 8-NOBIN, see: (a) Wang, Y.; Li, X.; Sun, J.; Ding. K. Organometallics 2003, 22, 1856; (b) Wang, Y.; Ji, B.; Ding, K. Chin. J. Chem. 2002, 20, 1300; (c) Wang, Y.; Li, X.; Ding, K. Tetrahedron Lett. 2002, 43, 159; (d) Guo, H.; Wang, Y.; Ding K. Chin. J. Chem. 2001, 19, 52; (e) Wang, Y.; Guo, H.; Ding, K. Tetrahedron: Asymmetry 2000, 11, 4153.
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