Highly effective synthesis of 4-halo-tetrahydropyrans via a highly diastereoselective in situ Prins-type cyclization reaction

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1627-1630

  Yang, Jun ^a   Viswanathan, Ganapathy S ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROTETRAHYDROPYRAN DERIVATIVE; ALDEHYDE; ALLYL ALCOHOL; ALLYL BROMIDE; ALLYL COMPOUND; INDIUM; INDIUM CHLORIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033605402     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00027-1     Document Type: Article

References (19)

1. 1. For reviews, see: Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 51, 505; Adams, D. R.; Bhatnagar, S. P. Synthesis, 1977, 661.
2. 1. For reviews, see: Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 51, 505; Adams, D. R.; Bhatnagar, S. P. Synthesis, 1977, 661.
3. 2. Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis, VCH Weinheim, 1996.
4. 3. Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999. For a review on indium mediated reactions, see: Cintas, P. Synlett, 1995, 1087; For additional information, see: Li, C. J. Tetrahedron, 1996, 52, 5643; Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, John Wiley & Sons, New York 1997; Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P.; Williamson, T. Eds, Oxford University Press: Oxford, 1998; Lubineau, A.; Auge, J.; Queneau, Y. in Organic Synthesis in Water, ed. Grieco, P. A. Blackie Academic & Professional, Glasgow, 1998.
5. 3. Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999. For a review on indium mediated reactions, see: Cintas, P. Synlett, 1995, 1087; For additional information, see: Li, C. J. Tetrahedron, 1996, 52, 5643; Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, John Wiley & Sons, New York 1997; Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P.; Williamson, T. Eds, Oxford University Press: Oxford, 1998; Lubineau, A.; Auge, J.; Queneau, Y. in Organic Synthesis in Water, ed. Grieco, P. A. Blackie Academic & Professional, Glasgow, 1998.
6. 3. Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999. For a review on indium mediated reactions, see: Cintas, P. Synlett, 1995, 1087; For additional information, see: Li, C. J. Tetrahedron, 1996, 52, 5643; Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, John Wiley & Sons, New York 1997; Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P.; Williamson, T. Eds, Oxford University Press: Oxford, 1998; Lubineau, A.; Auge, J.; Queneau, Y. in Organic Synthesis in Water, ed. Grieco, P. A. Blackie Academic & Professional, Glasgow, 1998.
7. 3. Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999. For a review on indium mediated reactions, see: Cintas, P. Synlett, 1995, 1087; For additional information, see: Li, C. J. Tetrahedron, 1996, 52, 5643; Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, John Wiley & Sons, New York 1997; Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P.; Williamson, T. Eds, Oxford University Press: Oxford, 1998; Lubineau, A.; Auge, J.; Queneau, Y. in Organic Synthesis in Water, ed. Grieco, P. A. Blackie Academic & Professional, Glasgow, 1998.
8. 3. Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999. For a review on indium mediated reactions, see: Cintas, P. Synlett, 1995, 1087; For additional information, see: Li, C. J. Tetrahedron, 1996, 52, 5643; Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, John Wiley & Sons, New York 1997; Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P.; Williamson, T. Eds, Oxford University Press: Oxford, 1998; Lubineau, A.; Auge, J.; Queneau, Y. in Organic Synthesis in Water, ed. Grieco, P. A. Blackie Academic & Professional, Glasgow, 1998.
9. 3. Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999. For a review on indium mediated reactions, see: Cintas, P. Synlett, 1995, 1087; For additional information, see: Li, C. J. Tetrahedron, 1996, 52, 5643; Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, John Wiley & Sons, New York 1997; Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P.; Williamson, T. Eds, Oxford University Press: Oxford, 1998; Lubineau, A.; Auge, J.; Queneau, Y. in Organic Synthesis in Water, ed. Grieco, P. A. Blackie Academic & Professional, Glasgow, 1998.
10. 4 . Identification and isolation of these compounds were initially carried out by G. S. Viswanathan in the author list.
11. 5. Such compounds were also accessible through titanium tetrachloride and aluminum trichloride catalyzed allylsilane reactions of aldehydes and realted cross-coupling between homoallyl alcohols and aldehydes. However, when both substituents are aromatic, the reaction provided no product or a low yield, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Perron, F.; Albizati, K. F. J. Org. Chem. 1987, 52, 4130; Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768; Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913. Very recently, Rychnovsky and co-workers developed a tin tetrabromide-mediated segment-coupling Prins cyclizations, see: Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
12. 5. Such compounds were also accessible through titanium tetrachloride and aluminum trichloride catalyzed allylsilane reactions of aldehydes and realted cross-coupling between homoallyl alcohols and aldehydes. However, when both substituents are aromatic, the reaction provided no product or a low yield, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Perron, F.; Albizati, K. F. J. Org. Chem. 1987, 52, 4130; Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768; Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913. Very recently, Rychnovsky and co-workers developed a tin tetrabromide-mediated segment-coupling Prins cyclizations, see: Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
13. 5. Such compounds were also accessible through titanium tetrachloride and aluminum trichloride catalyzed allylsilane reactions of aldehydes and realted cross-coupling between homoallyl alcohols and aldehydes. However, when both substituents are aromatic, the reaction provided no product or a low yield, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Perron, F.; Albizati, K. F. J. Org. Chem. 1987, 52, 4130; Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768; Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913. Very recently, Rychnovsky and co-workers developed a tin tetrabromide-mediated segment-coupling Prins cyclizations, see: Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
14. 5. Such compounds were also accessible through titanium tetrachloride and aluminum trichloride catalyzed allylsilane reactions of aldehydes and realted cross-coupling between homoallyl alcohols and aldehydes. However, when both substituents are aromatic, the reaction provided no product or a low yield, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Perron, F.; Albizati, K. F. J. Org. Chem. 1987, 52, 4130; Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768; Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913. Very recently, Rychnovsky and co-workers developed a tin tetrabromide-mediated segment-coupling Prins cyclizations, see: Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
15. 5. Such compounds were also accessible through titanium tetrachloride and aluminum trichloride catalyzed allylsilane reactions of aldehydes and realted cross-coupling between homoallyl alcohols and aldehydes. However, when both substituents are aromatic, the reaction provided no product or a low yield, see: Wei, Z. Y.; Li, J. S.; Wang, D.; Chan, T. H. Tetrahedron Lett. 1987, 28, 3441; Perron, F.; Albizati, K. F. J. Org. Chem. 1987, 52, 4130; Wei, Z. Y.; Wang, D.; Li, J. S.; Chan, T. H. J. Org. Chem. 1989, 54, 5768; Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913. Very recently, Rychnovsky and co-workers developed a tin tetrabromide-mediated segment-coupling Prins cyclizations, see: Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Tetrahedron Lett. 1998, 39, 7271.
16. 3 catalyzed reactions, see: Loh, T. P.; Wei, L. L. Tetrahedron Lett. 1998, 39, 323; Loh, T. P.; Chua, G. L.; Vittal, J. J.; Wong, M. W. Chem. Commun. 1998, 861; Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 39, 6291; Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.
17. 3 catalyzed reactions, see: Loh, T. P.; Wei, L. L. Tetrahedron Lett. 1998, 39, 323; Loh, T. P.; Chua, G. L.; Vittal, J. J.; Wong, M. W. Chem. Commun. 1998, 861; Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 39, 6291; Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.
18. 3 catalyzed reactions, see: Loh, T. P.; Wei, L. L. Tetrahedron Lett. 1998, 39, 323; Loh, T. P.; Chua, G. L.; Vittal, J. J.; Wong, M. W. Chem. Commun. 1998, 861; Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 39, 6291; Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.
19. 3 catalyzed reactions, see: Loh, T. P.; Wei, L. L. Tetrahedron Lett. 1998, 39, 323; Loh, T. P.; Chua, G. L.; Vittal, J. J.; Wong, M. W. Chem. Commun. 1998, 861; Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 39, 6291; Babu, G.; Perumal, P. T. Tetrahedron 1998, 54, 1627.