Enantioselective Michael addition reactions of malononitrile catalyzed by chiral Lewis acid and achiral amine catalysts

Tetrahedron Asymmetry

Volumn 14, Issue 6, 2003, Pages 635-639

  Itoh, Kennosuke ^a   Oderaotoshi, Yoji ^b   Kanemasa, Shuji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; LEWIS ACID; MALONONITRILE; OXAZOLIDINONE DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; PRIORITY JOURNAL; ROOM TEMPERATURE; X RAY CRYSTALLOGRAPHY;

EID: 0037459250     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00084-3     Document Type: Article

References (44)

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6. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
7. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
8. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
9. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
10. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
11. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
12. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
13. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
14. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
15. For the enantioselective Michael additions by donor activation, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. K.; Yokoyama, H.; Hayasaka, T.; Ebihara, K. J. Org. Chem. 1988, 53, 4148-4149; (b) Kumamoto, T.; Aoki, S.; Nakajima, M.; Koga, K. Tetrahedron: Asymmetry 1994, 5, 1431-1432; (c) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233-8236; (d) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520-3530 and references cited therein; (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119-120; (f) Alexakis, A.; Vastra, J.; Manganey, P. Tetrahedron Lett. 1997, 38, 7745-7748; (g) Alexakis, A.; Vastra, J.; Burton, J.; Manganey, P. Tetrahedron: Asymmetry 1997, 8, 3193-3196; (h) Bako, P.; Kiss, T.; Take, L. Tetrahedron Lett. 1997, 38, 7259-7262; (i) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442; (j) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
16. For enantioselective Michael additions of silyl enolates or ketene silyl acetals, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100 and references cited therein; (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924; (c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. Tetrahedron 1997, 53, 13009-13026; (d) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570; (e) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995; (f) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 11, 865-868; (g) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
17. For enantioselective Michael additions of silyl enolates or ketene silyl acetals, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100 and references cited therein; (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924; (c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. Tetrahedron 1997, 53, 13009-13026; (d) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570; (e) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995; (f) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 11, 865-868; (g) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
18. For enantioselective Michael additions of silyl enolates or ketene silyl acetals, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100 and references cited therein; (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924; (c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. Tetrahedron 1997, 53, 13009-13026; (d) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570; (e) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995; (f) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 11, 865-868; (g) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
19. For enantioselective Michael additions of silyl enolates or ketene silyl acetals, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100 and references cited therein; (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924; (c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. Tetrahedron 1997, 53, 13009-13026; (d) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570; (e) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995; (f) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 11, 865-868; (g) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
20. For enantioselective Michael additions of silyl enolates or ketene silyl acetals, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100 and references cited therein; (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924; (c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. Tetrahedron 1997, 53, 13009-13026; (d) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570; (e) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995; (f) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 11, 865-868; (g) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
21. For enantioselective Michael additions of silyl enolates or ketene silyl acetals, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100 and references cited therein; (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924; (c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. Tetrahedron 1997, 53, 13009-13026; (d) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570; (e) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995; (f) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 11, 865-868; (g) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480-4491.
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39. 2 did not show any catalytic activity either.
40. Bulky amines such as TMP should be less coordinating to the metallic center of R,R-DBFOX/Ph complexes so that deactivation of the Lewis acid catalyst is relatively avoided.
41. 8b.
42. When the catalytic amounts of amines were reduced, both catalytic activity and enantioselectivities were much decreased.
43. Sometimes, when reactions are performed under a lower temperature such as -40 to -78°C, unexpectedly low enantioselectivities result. The reason has remained unsolved.
44. Such intramolecular protonation has been involved in an enantioselective sequence of Michael addition/cyclization reactions of cyclic 1,3-diketones producing enol lactones under the double catalytic activation conditions. See: Ito, K.; Kanemasa, S., unpublished results.