Highly enantioselective homogeneous catalysis of chiral rare earth phosphates in the hetero-Diels-Alder reaction

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6129-6132

  Furuno, Hiroshi ^a   Kambara, Takeshi ^b   Tanaka, Yumiko ^a   Hanamoto, Takeshi ^a   Kagawa, Takumi ^b   Inanaga, Junji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOSOH CORPORATION   (Japan)

Author keywords

Asymmetric hetero Diels Alder reaction; Chiral rare earth metal phosphate; Lewis acid catalyst; Reusable catalyst

Indexed keywords

1,1' BINAPHTHYL 2,2' DIYLPHOSPHATE; ALDEHYDE; ALKADIENE; CARBONYL DERIVATIVE; LANTHANIDE; LEWIS ACID; METAL COMPLEX; PHENYLGLYOXYLIC ACID; PHOSPHATE; SCANDIUM; UNCLASSIFIED DRUG; YTTERBIUM; YTTRIUM;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; RECYCLING; ROOM TEMPERATURE;

BETULACEAE;

EID: 0037629594     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01460-6     Document Type: Article

References (28)

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2. For recent reviews, see: (a) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2225; (b) Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227-2302; (c) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850; (d) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem., Int. Ed. Engl. 2002, 41, 3554-3571.
3. For recent reviews, see: (a) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2225; (b) Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227-2302; (c) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850; (d) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem., Int. Ed. Engl. 2002, 41, 3554-3571.
4. For recent reviews, see: (a) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2225; (b) Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227-2302; (c) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850; (d) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem., Int. Ed. Engl. 2002, 41, 3554-3571.
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7. 3-catalyzed highly enantioselective Michael addition of O-alkylhydroxylamines to conjugated enones have also been reported: (a) Sugihara, H.; Daikai, K.; Jin, X. L.; Furuno, H.; Inanaga, J. Tetrahedron Lett. 2002, 43, 2735-2739; (b) Jin, X. L.; Sugihara, H.; Daikai, K.; Tateishi, H.; Jin, Y. Z.; Furuno, H.; Inanaga, J. Tetrahedron 2002, 58, 8321-8329; 2003, 59, 877.
8. 3-catalyzed highly enantioselective Michael addition of O-alkylhydroxylamines to conjugated enones have also been reported: (a) Sugihara, H.; Daikai, K.; Jin, X. L.; Furuno, H.; Inanaga, J. Tetrahedron Lett. 2002, 43, 2735-2739; (b) Jin, X. L.; Sugihara, H.; Daikai, K.; Tateishi, H.; Jin, Y. Z.; Furuno, H.; Inanaga, J. Tetrahedron 2002, 58, 8321-8329; 2003, 59, 877.
9. 3-catalyzed highly enantioselective Michael addition of O-alkylhydroxylamines to conjugated enones have also been reported: (a) Sugihara, H.; Daikai, K.; Jin, X. L.; Furuno, H.; Inanaga, J. Tetrahedron Lett. 2002, 43, 2735-2739; (b) Jin, X. L.; Sugihara, H.; Daikai, K.; Tateishi, H.; Jin, Y. Z.; Furuno, H.; Inanaga, J. Tetrahedron 2002, 58, 8321-8329; 2003, 59, 877.
10. For a recent review, see: Jørgensen K.A. Angew. Chem., Int. Ed. Engl. 39:2000;3558-3588.
11. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
12. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
13. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
14. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
15. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
16. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
17. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
18. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
19. For some recent examples of the enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 8, see: (a) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793-3798; (b) Yuan, Y.; Long, J.; Sun, J.; Ding, K. Chem. Eur. J. 2002, 8, 5033-5042; (c) Kii, S.; Hashimoto, T.; Maruoka, K. Synlett 2002, 931-932; (d) Wang, B.; Feng, X.; Huang, Y.; Liu, H.; Cui, X.; Jiang, Y. J. Org. Chem. 2002, 67, 2175-2182; (e) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10-11; (f) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366-5367; (g) Aikawa, K.; Irie, R.; Katsuki, T. Tetrahedron 2001, 57, 845-851; (h) Kezuka, S.; Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342; (i) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451-3454.
20. For some reported chiral catalysts containing octahydrobinaphthyl ring, see: Ref. 6d and (a) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681-684; (b) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. Engl. 2002, 41, 2348-2350; (c) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080-4081.
21. For some reported chiral catalysts containing octahydrobinaphthyl ring, see: Ref. 6d and (a) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681-684; (b) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. Engl. 2002, 41, 2348-2350; (c) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080-4081.
22. For some reported chiral catalysts containing octahydrobinaphthyl ring, see: Ref. 6d and (a) Boiteau, J.-G.; Imbos, R.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2003, 5, 681-684; (b) Hu, A.-G.; Fu, Y.; Xie, J.-H.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. Engl. 2002, 41, 2348-2350; (c) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080-4081.
23. Cram D.J., Helgeson R.C., Peacock S.C., Kaplan L.J., Domeier L.A., Moreau P., Koga K., Mayer J.M., Chao Y., Siegel M.G., Hoffman D.H., Sogah G.D.Y. J. Org. Chem. 43:1978;1930-1946.
24. Isolated yields of the complexes: By method A: 1-Sc, 92%; 1-Yb, 96%; 2-Yb, 94%; 3-Sc, 83%; 3-Yb, 80%. By method B: quantitative for all the complexes.
25. 2O: C, 60.91; H, 5.79. Found: C, 61.05; H, 5.45.
26. For the highly enantioselective hetero-Diels-Alder reaction of α-keto esters with the diene 8, see: (a) Dalko, P. I.; Moisan, L.; Cossy, J. Angew. Chem., Int. Ed. Engl. 2002, 41, 625-628; (b) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233; (c) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599-8605.
27. For the highly enantioselective hetero-Diels-Alder reaction of α-keto esters with the diene 8, see: (a) Dalko, P. I.; Moisan, L.; Cossy, J. Angew. Chem., Int. Ed. Engl. 2002, 41, 625-628; (b) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233; (c) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599-8605.
28. For the highly enantioselective hetero-Diels-Alder reaction of α-keto esters with the diene 8, see: (a) Dalko, P. I.; Moisan, L.; Cossy, J. Angew. Chem., Int. Ed. Engl. 2002, 41, 625-628; (b) Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233; (c) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599-8605.