A new cationic, chiral catalyst for highly enantioselective Diels-Alder reactions

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2465-2467

  Sprott, Kevin T ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHACROLEIN; CATION; CYCLOPENTADIENE DERIVATIVE; TRIOLEIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY;

CATALYSIS; CATIONS; STEREOISOMERISM;

EID: 0141519638     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034706k     Document Type: Article

References (27)

1. For recent reviews, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, p 1177. (c) Diaz, L. C. J. Braz. Chem. Soc. 1997, 2, 289. (d) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 488. (e) Ishihara, K.; Yamamoto, H. Eur. J. Chem. 1999, 527.
2. For recent reviews, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, p 1177. (c) Diaz, L. C. J. Braz. Chem. Soc. 1997, 2, 289. (d) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 488. (e) Ishihara, K.; Yamamoto, H. Eur. J. Chem. 1999, 527.
3. For recent reviews, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, p 1177. (c) Diaz, L. C. J. Braz. Chem. Soc. 1997, 2, 289. (d) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 488. (e) Ishihara, K.; Yamamoto, H. Eur. J. Chem. 1999, 527.
4. For recent reviews, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, p 1177. (c) Diaz, L. C. J. Braz. Chem. Soc. 1997, 2, 289. (d) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 488. (e) Ishihara, K.; Yamamoto, H. Eur. J. Chem. 1999, 527.
5. For recent reviews, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, p 1177. (c) Diaz, L. C. J. Braz. Chem. Soc. 1997, 2, 289. (d) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 488. (e) Ishihara, K.; Yamamoto, H. Eur. J. Chem. 1999, 527.
6. Corey, E. J.; Lee, T. W. J. Chem. Soc., Chem. Commun. 2001, 1321.
7. See: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502. (b) Corey E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. (c) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992. (d) Bruin, M. E.; Kündig, E. P. J. Chem. Soc., Chem. Commun. 1998, 2635. (e) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220.
8. See: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502. (b) Corey E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. (c) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992. (d) Bruin, M. E.; Kündig, E. P. J. Chem. Soc., Chem. Commun. 1998, 2635. (e) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220.
9. See: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502. (b) Corey E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. (c) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992. (d) Bruin, M. E.; Kündig, E. P. J. Chem. Soc., Chem. Commun. 1998, 2635. (e) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220.
10. See: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502. (b) Corey E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. (c) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992. (d) Bruin, M. E.; Kündig, E. P. J. Chem. Soc., Chem. Commun. 1998, 2635. (e) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220.
11. See: (a) Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502. (b) Corey E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808. (c) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992. (d) Bruin, M. E.; Kündig, E. P. J. Chem. Soc., Chem. Commun. 1998, 2635. (e) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220.
12. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
13. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
14. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
15. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
16. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
17. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
18. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
19. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
20. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
21. For previous syntheses, see: (a) Clive, D. L. J.; Anderson, P. C.; Moss, N.; Singh, A. J. Org. Chem. 1982, 47, 1641. (b) De Meijere, A.; Stecker, B.; Kourdioukov, A.; Williams, C. M. Synthesis 2000, 929. (c) Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F. G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289. (d) Ishiyama, T.; Ahiko, T.-A.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889. (e) Lutz, R. P.; Berg, H. A. J. J. Org. Chem. 1980, 45, 3915. (f) Orita, A.; Watanabe, A.; Tsuchiya, H.; Otera, J. Tetrahedron 1999, 55, 2889. (g) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. (h) Sasaoka, S.; Yamamoto, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 315. (i) Sjoholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc., Chem. Commun. 1994, 1217. (j) Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yasue, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1263.
22. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
23. The use of hexanes as cosolvent and the addition of a solution of the substrate 4 in hexanes to the well-stirred reaction mixture are essential to efficient bis-dihydroxylation.
24. The enantiomeric purity of the tetraol 5 was determined by HPLC analysis at 23°C using a Chiracel AD column with 1% isopropyl alcohol in hexanes (retention time for 5 16.7 min; retention times for the corresponding racemate 18.3 and 16.7 min; retention times for the corresponding 5,6-diastereomeric racemate 19.9 and 21.7 min).
25. N2 reaction of this amino mesylate would then lead to cis-N-benzyl-2,5-dibenzylpyrrolidine.
26. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
27. f = 0.28.