Catalytic enantioselective synthesis of 2,6-disubstituted dihydropyrones by hetero-Diels-Alder reaction using chiral BINOL-Ti(IV) complex

Synlett

Volumn , Issue 12, 2002, Pages 2122-2124

  Huang, Yaozong ^b   Feng, Xiaoming ^a   Wang, Bin ^b   Zhang, Guolin ^c   Jiang, Yaozhong ^b  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

BINOL; Dihydropyrones; Hetero Diels Alder reaction

Indexed keywords

DIHYDROPYRONE DERIVATIVE; METAL COMPLEX; PYRONE DERIVATIVE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; OPTICAL ROTATION; SYNTHESIS;

EID: 0036458157     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35607     Document Type: Article

References (26)

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2. For reviews, see: (a) Danishefsky, S. J. Chemtracts 1989, 273. (b) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (c) Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. (d) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558; for application in total synthesis. (e) Rainier, J. D.; Allwein, S. P.; Cox, J. M. Org. Lett. 2000, 2, 231.
3. For reviews, see: (a) Danishefsky, S. J. Chemtracts 1989, 273. (b) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (c) Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. (d) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558; for application in total synthesis. (e) Rainier, J. D.; Allwein, S. P.; Cox, J. M. Org. Lett. 2000, 2, 231.
4. For reviews, see: (a) Danishefsky, S. J. Chemtracts 1989, 273. (b) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (c) Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. (d) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558; for application in total synthesis. (e) Rainier, J. D.; Allwein, S. P.; Cox, J. M. Org. Lett. 2000, 2, 231.
5. For reviews, see: (a) Danishefsky, S. J. Chemtracts 1989, 273. (b) Danishefsky, S. J.; De Ninno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15. (c) Danishefsky, S. J. Aldrichimica Acta 1986, 19, 59. (d) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558; for application in total synthesis. (e) Rainier, J. D.; Allwein, S. P.; Cox, J. M. Org. Lett. 2000, 2, 231.
6. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
7. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
8. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
9. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
10. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
11. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
12. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
13. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
14. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
15. For hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes, see: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (b) Togni, A. Organometallics 1990, 9, 3106. (c) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (d) Gao, Q.; Ishihara, K.; Maruyarna, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (e) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998. (f) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79. (g) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403. (h) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 123. (i) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366. (j) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10.
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21. 8-BINOL-Ti(IV) catalytic system could give better enantioselectivity and diastereoselectivity than (R)-BINOL-Ti(IV) complex.
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