Indium-trichloride mediated synthesis of 4,4-dichlorotetrahydropyrans

Synlett

Volumn , Issue 6, 1999, Pages 717-718

  Yang, Jun ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

4,4 dichlorotetrahydropyran; Gem dihalide; Indium trichloride; Prins reaction

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; INDIUM CHLORIDE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033040770     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2707     Document Type: Article

References (25)

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2. For reviews on indium-mediated reactions, see: Cintas, P. Synlett, 1995, 1087; Hashmi, A.S.K.; J. Prakt. Chem., Chem. Zeit. 1998, 340, 84.
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5. For reviews, 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; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741; Li, C. J. Chem. Rev. 1993, 93, 2023; 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.
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9. For reviews, 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; Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741; Li, C. J. Chem. Rev. 1993, 93, 2023; 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.
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13. Gabbai, F. P.; Schier, A.; Riede, J.; Schichl, D. Organometallics 1996, 15, 4119; Babu, G.; Perumal, P.T.; Tetrahedron Lett. 1997, 38, 5025; Loh, T. P.; Wei, L. Tetrahedron 1998, 54, 26; Ranu, B. C.; Dutta, P.; Sarkar, A. J. Org. Chem. 1998, 63, 6027.
14. Gabbai, F. P.; Schier, A.; Riede, J.; Schichl, D. Organometallics 1996, 15, 4119; Babu, G.; Perumal, P.T.; Tetrahedron Lett. 1997, 38, 5025; Loh, T. P.; Wei, L. Tetrahedron 1998, 54, 26; Ranu, B. C.; Dutta, P.; Sarkar, A. J. Org. Chem. 1998, 63, 6027.
15. For examples, Loh, T. P.; Pei, J.; Cao, G. Q. Chem. Commun. 1996, 1819; Loh, T. P.; Pei, J.; Lin, M. Chem. Commun. 1996, 2315; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535; Loh, T. P.; Wei, L. L. Synlett 1998, 975; Loh, T. P.; Xu, K. C.; Ho, D. S. C.; Sim, K. Y. Synlett 1998, 369.
16. For examples, Loh, T. P.; Pei, J.; Cao, G. Q. Chem. Commun. 1996, 1819; Loh, T. P.; Pei, J.; Lin, M. Chem. Commun. 1996, 2315; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535; Loh, T. P.; Wei, L. L. Synlett 1998, 975; Loh, T. P.; Xu, K. C.; Ho, D. S. C.; Sim, K. Y. Synlett 1998, 369.
17. For examples, Loh, T. P.; Pei, J.; Cao, G. Q. Chem. Commun. 1996, 1819; Loh, T. P.; Pei, J.; Lin, M. Chem. Commun. 1996, 2315; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535; Loh, T. P.; Wei, L. L. Synlett 1998, 975; Loh, T. P.; Xu, K. C.; Ho, D. S. C.; Sim, K. Y. Synlett 1998, 369.
18. For examples, Loh, T. P.; Pei, J.; Cao, G. Q. Chem. Commun. 1996, 1819; Loh, T. P.; Pei, J.; Lin, M. Chem. Commun. 1996, 2315; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535; Loh, T. P.; Wei, L. L. Synlett 1998, 975; Loh, T. P.; Xu, K. C.; Ho, D. S. C.; Sim, K. Y. Synlett 1998, 369.
19. For examples, Loh, T. P.; Pei, J.; Cao, G. Q. Chem. Commun. 1996, 1819; Loh, T. P.; Pei, J.; Lin, M. Chem. Commun. 1996, 2315; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535; Loh, T. P.; Wei, L. L. Synlett 1998, 975; Loh, T. P.; Xu, K. C.; Ho, D. S. C.; Sim, K. Y. Synlett 1998, 369.
20. Yang, J.; Viswanathan, G.S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; For a catalytic Prins cyclization, see: Zhang, W. C.; Viswanathan, G.S.; Li, C. J. Chem. Commun. 1999, 291.
21. Yang, J.; Viswanathan, G.S.; Li, C. J. Tetrahedron Lett. 1999, 40, 1627; For a catalytic Prins cyclization, see: Zhang, W. C.; Viswanathan, G.S.; Li, C. J. Chem. Commun. 1999, 291.
22. Yi, X.-H.; Meng, Y.; Li, C. J. Tetrahedron Lett. 1997, 38, 4731; Li, C.J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017.
23. Yi, X.-H.; Meng, Y.; Li, C. J. Tetrahedron Lett. 1997, 38, 4731; Li, C.J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017.
24. 2O: C, 66.5; H, 5.2; Found: C, 66.9; H, 5.4.
25. 2O: C, 65.7; H, 8.0. Found: C, 65.5; H, 8.6.