Scandium triflate catalyzed in situ Prins-type cyclization: Formations of 4-tetrahydropyranols and ethers

Chemical Communications

Volumn , Issue 3, 1999, Pages 291-292

  Zhang, Wen Chun ^a   Viswanathan, Ganapathy S ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ETHER DERIVATIVE; SCANDIUM; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; ORGANIC CHEMISTRY;

EID: 0033531360     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808960d     Document Type: Article

References (16)

1. For reviews, see: E. Arundale and L. A. Mikeska, Chem. Rev., 1952, 51, 505; D. R. Adams and S. P. Bhatnagar, Synthesis, 1977, 661.
2. For reviews, see: E. Arundale and L. A. Mikeska, Chem. Rev., 1952, 51, 505; D. R. Adams and S. P. Bhatnagar, Synthesis, 1977, 661.
3. K. C. Nicolaou and E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
4. The best known method in this regard is probably the hetero-Diels-Alder reaction with Danishefsky's diene; for examples, see: S. J. Danishefsky, W. H. Pearson and D. F. Harvey, J. Am. Chem. Soc., 1984, 106, 2456; S. J. Danishefsky and C. J. Maring, J. Am. Chem. Soc., 1989, 111, 2193.
5. The best known method in this regard is probably the hetero-Diels-Alder reaction with Danishefsky's diene; for examples, see: S. J. Danishefsky, W. H. Pearson and D. F. Harvey, J. Am. Chem. Soc., 1984, 106, 2456; S. J. Danishefsky and C. J. Maring, J. Am. Chem. Soc., 1989, 111, 2193.
6. X. H. Yi, J. X. Haberman and C. J. Li, Synth. Commun., 1998, 28, 2999.
7. 4-mediated segment-coupling Prins cyclization, see: S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39, 7271.
8. 4-mediated segment-coupling Prins cyclization, see: S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39, 7271.
9. 4-mediated segment-coupling Prins cyclization, see: S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39, 7271.
10. 4-mediated segment-coupling Prins cyclization, see: S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39, 7271.
11. 4-mediated segment-coupling Prins cyclization, see: S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39, 7271.
12. 4-mediated segment-coupling Prins cyclization, see: S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39, 7271.
13. For a leading reference, see: S. Kobayashi and I. Hachiya, J. Org. Chem., 1994, 59, 3590; For a related review, see: S. Kobayashi, Synlett, 1994, 689.
14. For a leading reference, see: S. Kobayashi and I. Hachiya, J. Org. Chem., 1994, 59, 3590; For a related review, see: S. Kobayashi, Synlett, 1994, 689.
15. 3 catalyzed allylation of aldehydes with allylsilane to generate homoallyl alcohols, see: Y. Yang, M. Wang and D. Wang, Chem. Commun., 1997, 1651.
16. J. Nokami, K. Yoshizane, H. Matsuura and S. Sumida, J. Am. Chem. Soc., 1998, 120, 6609.