Asymmetric base catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral acrylate derivatives

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1211-1214

  Okamura, Hiroaki ^a   Morishige, Katsuki ^a   Iwagawa, Tetsuo ^a   Nakatani, Munehiro ^a  

^a KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CINCHONA ALKALOID; CINCHONIDINE; CINCHONINE; OXAZOLIDINONE DERIVATIVE; QUINIDINE;

ARTICLE; CATALYST; DIASTEREOISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032485521     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10843-7     Document Type: Article

References (14)

1. 1. K. Afarinkia, V. Vinader, T. D. Nelson, and G. H. Posner, Tetrahedron, 1992, 48, 9111-9171; J. A. Gladysz, S. J. Lee, J. A. V. Tomasello, and Y. S. Yu, J. Org. Chem., 1977, 42, 4170-4172.; V. Prapansiri and E. R. Thoronton, Tetrahedron Lett., 1991, 32, 3147-3150.; K. Narasaka, S. Shimada, K. Osoda, and N. Iwasawa, Synthesis, 1991, 1171-1172.; K. C. Nicolaou, J. J. Liu, C.-K. Hwang, W.-M. Dai, and R. K. Guy, J. Chem. Soc., Chem. Commun., 1992, 1118-1120.
2. 1. K. Afarinkia, V. Vinader, T. D. Nelson, and G. H. Posner, Tetrahedron, 1992, 48, 9111-9171; J. A. Gladysz, S. J. Lee, J. A. V. Tomasello, and Y. S. Yu, J. Org. Chem., 1977, 42, 4170-4172.; V. Prapansiri and E. R. Thoronton, Tetrahedron Lett., 1991, 32, 3147-3150.; K. Narasaka, S. Shimada, K. Osoda, and N. Iwasawa, Synthesis, 1991, 1171-1172.; K. C. Nicolaou, J. J. Liu, C.-K. Hwang, W.-M. Dai, and R. K. Guy, J. Chem. Soc., Chem. Commun., 1992, 1118-1120.
3. 1. K. Afarinkia, V. Vinader, T. D. Nelson, and G. H. Posner, Tetrahedron, 1992, 48, 9111-9171; J. A. Gladysz, S. J. Lee, J. A. V. Tomasello, and Y. S. Yu, J. Org. Chem., 1977, 42, 4170-4172.; V. Prapansiri and E. R. Thoronton, Tetrahedron Lett., 1991, 32, 3147-3150.; K. Narasaka, S. Shimada, K. Osoda, and N. Iwasawa, Synthesis, 1991, 1171-1172.; K. C. Nicolaou, J. J. Liu, C.-K. Hwang, W.-M. Dai, and R. K. Guy, J. Chem. Soc., Chem. Commun., 1992, 1118-1120.
4. 1. K. Afarinkia, V. Vinader, T. D. Nelson, and G. H. Posner, Tetrahedron, 1992, 48, 9111-9171; J. A. Gladysz, S. J. Lee, J. A. V. Tomasello, and Y. S. Yu, J. Org. Chem., 1977, 42, 4170-4172.; V. Prapansiri and E. R. Thoronton, Tetrahedron Lett., 1991, 32, 3147-3150.; K. Narasaka, S. Shimada, K. Osoda, and N. Iwasawa, Synthesis, 1991, 1171-1172.; K. C. Nicolaou, J. J. Liu, C.-K. Hwang, W.-M. Dai, and R. K. Guy, J. Chem. Soc., Chem. Commun., 1992, 1118-1120.
5. 1. K. Afarinkia, V. Vinader, T. D. Nelson, and G. H. Posner, Tetrahedron, 1992, 48, 9111-9171; J. A. Gladysz, S. J. Lee, J. A. V. Tomasello, and Y. S. Yu, J. Org. Chem., 1977, 42, 4170-4172.; V. Prapansiri and E. R. Thoronton, Tetrahedron Lett., 1991, 32, 3147-3150.; K. Narasaka, S. Shimada, K. Osoda, and N. Iwasawa, Synthesis, 1991, 1171-1172.; K. C. Nicolaou, J. J. Liu, C.-K. Hwang, W.-M. Dai, and R. K. Guy, J. Chem. Soc., Chem. Commun., 1992, 1118-1120.
6. 2. For preparation of 3-hydroxy-2-pyrone, see: J. A. Profitt, T. Jonse, and D. S. Watt, Synthetic Commn., 1975, 5, 457-460.
7. 3. H. Okamura, T. Iwagawa, and M. Nakatani, Tetrahedron Lett., 1995, 30, 5939-5942.
8. 4. H. Okamura, Y. Nakamura, T. Iwagawa, and M. Nakatani, Chem. Lett., 1996, 193-194.
9. 5. For excellent review of chiral auxiliaries see: D. A. Evans, Aldrichimica Acta, 1982, 15, 318-327.
10. 6. Chiral auxiliaries of 2a-c were derived from D-phenylglycinol, L-valinol, and (+)-norepedrine, respectively.
11. 7. S. Masamune, W. Choy, J. S. Petersen, and L. R. Sita, Angew. Chem., Int. Ed. Engl., 1985, 24, 1.
12. 28 = -38.5, mp. 84-86°C) from 3a. A detailed report of the asymmetric synthesis of pseudo-sugar is being preparing for publication.
13. 9. K. Tadano, H. Maeda, M. Hoshino, Y. Iimura, and T. Suami, J. Org. Chem., 1987, 52, 1946-1956.
14. 28 = +40).