Facile and efficient method for the Prins reactions of styrenes and homoallyl alcohols to 1,3-dioxanes and 4-tetrahydropyranols using bismuth(III) triflate

Synthetic Communications

Volumn 35, Issue 9, 2005, Pages 1177-1182

  Sreedhar, B ^a   Swapna, V ^a   Sridhar, Ch ^a   Saileela, D ^a   Sunitha, A ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,3 dioxanes; Bismuth(III) inflate; Homoallyl alcohols; Prins reaction; Tetrahydropyran 4 ol

Indexed keywords

1,3 DIOXANE DERIVATIVE; 4 TETRAHYDROPYRANOL; ALCOHOL; ALCOHOL DERIVATIVE; BISMUTH DERIVATIVE; BISMUTH TRIFLATE; HOMOALLYL ALCOHOL; PYRAN DERIVATIVE; STYRENE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; PRINS REACTION; SYNTHESIS;

EID: 18744399289     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200054759     Document Type: Article

References (22)

1. (a) Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in organic synthesis. Butterworths: London, 1987; 216;
2. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Aruyama, K. Versatile roles of Lewis acids in the reactions of allylic tin compounds. Tetrahedron 1993, 49, 7395;
3. (c) Yamamoto, Y.; Asao, N. Selective reactions using allylic metals. Chem. Rev. 1993, 93, 2207.
4. Prins, H. J. Chem. Weekbl. 1919, 16, 1072.
5. (a) Delmas, M. Selective synthesis of 4-aryl-1,3-dioxanes from arylalkenes and paraformaldehyde using an ion exchange resin as catalyst; extension to natural compounds. Synthesis 1980, 871;
6. n+- mont)-catalyzed Prins reaction. Bull. Chem. Soc. Jpn. 1996, 69, 2361;
7. (c) Bach, T.; Lobel, J. Selective Prins reaction of styrenes and formaldehyde catalyzed by 2,6-di-tert-butylphenoxy(difluoro)borane. Synthesis 2002, 17, 2521.
8. (a) Rychnovsky, S. D.; Hu, Y.; Ellsworth, B. Segment-coupling Prins cyclizations. Tetrahedron Lett. 1998, 39, 7271;
9. (b) Ghosh, A. K.; Shin, D.; Schiltz, G. Heterocycles 2002, 58, 659.
10. Nicolaou, K. C.; Sorenson, E. J. Classics in total synthesis. VCH: Weinheim, 1996.
11. (a) Repichet, S.; Leroux, C.; Hernandez, P.; Dubac, J.; Demurs, J. R. Bismuth(III) trifluoromethanesulfonate: An efficient catalyst for the sulfonylation of arenes. J. Org. Chem. 1999, 64, 6479;
12. (b) Repichet, S.; Le Roux, C.; Dubac, J. Bismuth(III) halides: Remarkable doping agents for triflic acid in the catalytic sulfonylation of arenes. Tetrahedron Lett. 1999, 40, 9233;
13. (c) Laurent-Robert, H.; Le Roux, C.; Dubac, J. Enhancement of dienophilic and enophilic reactivity of the glyoxylic acid by bismuth(III) triflate in the presence of water. Synlett 1998, 1138;
14. (d) Garrigues, B.; Gonzaga, F.; Robert, H.; Dubac, J. Bismuth(III) chloride or triflate-catalyzed dienophilic activity of α-ethylenic aldehydes and ketones J. Org. Chem. 1997, 62, 4880;
15. (e) Robert, H.; Garrigues, B.; Dubac, J. The carbonyl Diels-Alder reaction catalyzed by bismuth (III) chloride. Tetrahedron Lett. 1998, 39, 1161;
16. (f) Yanagisawa, A.; Morodome, M.; Nakashima, H.; Yamamoto, H. Allylation of aldehydes with allyltin compounds in acidic aqueous media - A catalytic version. Synlett 1997, 1309;
17. (g) Loh, T. P.; Xu, J. Trifluoromethane sulphonic acid: A Brönsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water. Tetrahedron Lett. 1999, 40, 2431.
18. (a) Choudary, B. M.; Chidara, S.; Sekhar, Ch. V. R. Highly efficient allylation of aldehydes and three-component synthesis of homoallylamines using bismuth triflate catalyst. Synlett 2002, 10, 1694;
19. (b) Choudary, B. M.; Sridhar, Ch. Sateesh, M.; Sreedhar, B. Microencapsulated bismuth(III) triflate for organic transformations. J. Mol. Cat. 2004, 212, 237-243.
20. Repichet, S.; Zwick, A.; Vendier, L.; Le Roux, C.; Dubac, J. A practical, cheap and environmentally friendly preparation of bismuth(III) trifluoromethanesulfonate. Tetrahedrron Lett. 2002, 43, 993.
21. n+-Mont)-catalyzed Prins reaction. Bull. Chem. Soc. Jpn. 1996, 69, 2361.
22. Bach, T.; Lobel, J. Selective Prins reaction of styrenes and formaldehyde catalyzed by 2,6-di-tert-butylphenoxy(difluoro)borane. Synthesis 2002, 17, 2521.