Enantioselective Heck-type hydroarylation of norbornene with phenyl iodide catalyzed by palladium/quinolinyl-oxazolines

Tetrahedron Asymmetry

Volumn 11, Issue 6, 2000, Pages 1255-1257

  Wu, Xin Yan ^a   Xu, Hua Dong ^a   Zhou, Qi Lin ^a,b   Chan, Albert S C ^c  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b NANKAI UNIVERSITY   (China)

^c HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; IODIDE; NORBORNENE DERIVATIVE; OXAZOLINE DERIVATIVE; PALLADIUM COMPLEX; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034616253     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00067-7     Document Type: Article

References (22)

1. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Org. React. 1982, 27, 345. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
2. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Org. React. 1982, 27, 345. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
3. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Org. React. 1982, 27, 345. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
4. Heck, R. F. Acc. Chem. Res. 1979, 12, 146. Heck, R. F. Org. React. 1982, 27, 345. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
5. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
6. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
7. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
8. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
9. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
10. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
11. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
12. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
13. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
14. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun. 1994, 1323. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315. Ashimori, A.; Bachand, B.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6477. Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488. Shibasaki, M.; Vogl, E. M. J. Organomet. Chem. 1999, 576, 1. Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 16.
15. Brunner, H.; Kramler, K. Synthesis 1991, 1121.
16. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927.
17. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 927.
18. Kauffmann reported up to 82.4% ee in the same reaction using Achiwa's ligand, but the yields are very low. See: Namyslo, J. C.; Kaufmann, D. E. Chem. Ber./Recueil 1997, 130, 1327.
19. Wu, X.-Y.; Li, X.-H.; Zhou, Q.-L. Tetrahedron: Asymmetry 1998, 9, 4143.
20. Prepared by Takahashi method: Takahashi, Y.; Ito, T.; Ishii, Y. Chem. Commun. 1970, 1065.
21. Proton sponge: 1,8-bis(dimethylamino)naphthalene.
22. Brunner, H.; Obermann, U.; Wimmer, P. J. Organomet. Chem. 1986, 316, C1.