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TMSI-mediated Prins-type Reaction of Epoxides with Homoallylic Alcohols: Synthesis of Iodo-Substituted Tetrahydropyrans

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Author Affiliations

  • 1Custom Pharmaceutical Services, Dr Reddy\'s Laboratories Limited, Bollaram Road, Miyapur, Hyderabad, 500049, India and Department of Organic Chemistry, Foods, Drugs and Water, Andhra University, Visakhapatnam, 530003, India
  • 2Ragas Pharmaceuticals Private Limited (OPC), IDA Cherlapally, Hyderabad, 500051, India
  • 3Custom Pharmaceutical Services, Dr Reddy\'s Laboratories Limited, Bollaram Road, Miyapur, Hyderabad, 500049, India
  • 4Department of Organic Chemistry, Foods, Drugs and Water, Andhra University, Visakhapatnam, 530003, India

Res.J.chem.sci., Volume 6, Issue (10), Pages 48-50, October,18 (2016)

Abstract

The cyclization of epoxides with homoallylic alcohols in the presence of Trimethylsilyliodide generates the 4-iodo-tetrahydropyran derivatives in excellent yield.

References

  1. Clarke P.A. and Santos S. (2006)., Strategies for the Formation of Tetrahydropyran Rings in the Synthesis of Natural Products., Eur. J. Org. Chem., 2006 (9), 2045-2053.
  2. Miranda P.O., Carballo R.M., Martín V.S. and Padrón J.I. (2009)., A New Catalytic Prins Cyclization Leading to Oxa- and Azacycles., Org. Lett., 11(2), 357-360.
  3. Liu F. and Loh T.P. (2007)., Highly Stereoselective Prins Cyclization of (Z)- and (E)-γ-Brominated Homoallylic Alcohols to 2,4,5,6-Tetrasubstituted Tetrahydropyrans., Org. Lett., 9(11), 2063-2066.
  4. Hu X.H., Liu F. and Loh T.P. (2009)., Stereoelectronic versus Steric Tuning in the Prins Cyclization Reaction: Synthesis of 2,6-trans Pyranyl Motifs., Org. Lett., 11(8), 1741-1743.
  5. Meilert K. and Brimble M.A. (2005)., Synthesis of the Bis-spiroacetal Moiety of Spirolides B and D., Org. Lett., 7(16), 3497-3500.
  6. Dziedzic M. and Furman B. (2008)., An efficient approach to the stereoselective synthesis of 2,6-disubstituted dihydropyrans via stannyl-Prins cyclization., Tetrahedron Lett., 49(4), 678-681.
  7. Lian Y. and Hinkle R.J. (2006)., BiBr3-Initiated Tandem Addition/Silyl-Prins Reactions to 2,6-Disubstituted Dihydropyrans., J. Org. Chem., 71(18), 7071-7074.
  8. Miranda P.O., Díaz D.D., Padrón J.I., Ramírez M.A. and Martín V. S. (2005)., Fe (III) Halides as Effective Catalysts in Carbon−Carbon Bond Formation:  Synthesis of 1,5-Dihalo-1,4-dienes, α,β-Unsaturated Ketones, and Cyclic Ethers., J. Org. Chem., 70(1), 57-62.
  9. Miranda P.O., Ramírez M.A., Martín V.S. and Padrón J.I. (2006)., The Silylalkyne-Prins Cyclization:  Stereoselective Synthesis of Tetra- and Pentasubstituted Halodihydropyrans., Org. Lett., 8(8), 1633-1636.
  10. Dobbs A.P., Parker R.J. and Skidmore J. (2008)., Rapid access to CF3-containing heterocycles., Tetrahedron Lett., 49 (5), 827-831.
  11. Overman L.E. and Velthuisen E.J. (2006)., Scope and Facial Selectivity of the Prins-Pinacol Synthesis of Attached Rings., J. Org. Chem., 71(4), 1581-1587.
  12. Jasti R., Anderson C.D. and Rychnovsky S.D. (2005)., Utilization of an Oxonia-Cope Rearrangement as a Mechanistic Probe for Prins Cyclizations., J. Am. Chem. Soc., 127(27), 9939-9945.
  13. Jasti R. and Rychnovsky S.D. (2006)., Racemization in Prins Cyclization Reactions., J. Am. Chem. Soc., 128(41), 13640-13648.
  14. Arundale E. and Mikeska L.A. (1952)., The Olefin-Aldehyde Condensation. The Prins Reaction., Chem. Rev., 51(3), 505-555.
  15. Adams D.R. and Bhatnagar S.P. (1977)., The Prins Reaction., Synthesis, 10, 661-672.
  16. Trost B.M., Fleming I. and Heathcock C.H. (1991)., In The Prins Reaction and Carbonyl Ene Reactions., Pergamon Press, New York, 527-561.
  17. Overman L.E. and Pennington L.D. (2003)., Strategic Use of Pinacol-Terminated Prins Cyclizations in Target-Oriented Total Synthesis., J. Org. Chem., 68 (19), 7143-7157.
  18. Pastor I. M. and Yus M. (2007)., The Prins Reaction: Advances and Applications., Curr. Org. Chem., 11 (10), 925-957.
  19. Dobbs A.P., Guesné S.J.J., Martinović S., Coles S.J. and Hursthouse M.B. (2003)., A Versatile Indium Trichloride Mediated Prins-Type Reaction to Unsaturated Heterocycles., J. Org. Chem., 68(20), 7880-7883.
  20. Dobbs A.P., Guesné S.J.J., Parker R.J., Skidmore J., Stephenson R.A. and Hursthouse M.B. (2010)., A detailed investigation of the aza-Prins reaction., Org. Biomol. Chem., 5(8), 1064-1080.
  21. Murty M.S.R., Rajasekhar K., Harikrishna V. and Yadav J.S. (2008)., Bismuth Triflate Catalyzed Prins-Type Cyclization in Ionic Liquid: Synthesis of 4-Tetrahydropyranol Derivatives., Heteroatom Chemistry, 19(1), 104-106.
  22. Murty M.S.R., Rajasekhar K. and Yadav J.S. (2006)., ZrCl4 mediated cyclization between epoxides and homopropargylic alcohols: synthesis of 4-chloro-5,6-dihydro-2H-pyran derivatives., Tetrahedron Lett., 47 (34), 6149-6151.
  23. Yadav J.S., Subba Reddy B.V., Ramesh K., Narayana Kumar G.G.K.S. and René Grée. (2010)., An expeditious synthesis of 4-fluoropiperidines via aza-Prins cyclization., Tetrahedron Lett., 51 (12), 1578-1581.
  24. Chavre S.N., Choo H., Lee J.K., Pae A.N., Kim Y. and Cho Y.S. (2008)., 5- and 6-Exocyclic Products, cis-2,3,5-Trisubstituted Tetrahydrofurans, and cis-2,3,6-Trisubstituted Tetrahydropyrans via Prins-Type Cyclization., J. Org. Chem., 73(19), 7467-7471.
  25. Tian G.-Q. and Shi M. (2007)., Brønsted Acid-Mediated Stereoselective Cascade Construction of Functionalized Tetrahydropyrans from 2-(Arylmethylene) cyclopropylcarbinols and Aldehydes., Org. Lett., 9(12), 2405-2408.
  26. Jianke Li. and Chao-Jun Li. (2001)., Synthesis of tetrahydropyran derivatives via a novel indium trichloride mediated cross-cyclization between epoxides and homoallyl alcohols., Tetrahedron Lett., 42(5), 793-796.
  27. Murty M.S.R., Rajasekhar K. and Yadav J.S. (2005)., ZrCl4 mediated cross-cyclization between epoxides and homoallylic alcohols: synthesis of 4-chlorotetrahydropyran derivatives., Tetrahedron Lett., 46(13), 2311–2314.
  28. Murty M.S.R., Rajasekhar K. and Yadav J.S. (2005)., Mild and Efficient Method for the Synthesis of Tetrahydropyran Derivatives via Cross-Cyclization between Epoxides and Homoallylic Alcohols Mediated by Bismuth(III) Chloride., Synlett., 12, 1945-1947.
  29. Sabitha Gowravaram, Bhaskar Reddy K., Bhikshapathi M. and Yadav J.S. (2006)., TMSI mediated Prins-type cyclization of ketones with homoallylic and homopropargylic alcohol: synthesis of 2,2-disubstituted-, spirocyclic-4-iodo-tetrahydropyrans and 5,6-dihydro-2H-pyrans., Tetrahedron Lett., 47(16), 2807-2810.
  30. Ollevier T. and Lavie-Compin G. (2004)., Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions., Tetrahedron Lett., 45(1), 49-52.
  31. Baltork M. and Aliyan H. (1998)., Bismuth(III) Chloride; A Mild and Efficient Catalyst for Synthesis of Thiiranes from Oxiranes., Synth. Commun., 28(21), 3943-3948.
  32. Baltork M., Tangestaninejad S., Aliyan H. and Mirkhani V. (2000)., Bismuth (III) Chloride (BiCl3); An Efficient Catalyst for Mild, Regio- and Stereoselective Cleavage of Epoxides with Alcohols, Acetic Acid and Water., Synth. Commun., 30(13), 2365-2374.
  33. Baltork M., Khosropour A.R. and Aliyan H. (2001)., Efficient conversion of epoxides to 1,3-dioxolanes catalyzed by Bismuth (III) salts., Synth. Commun., 31(22), 3411-3416.
  34. Swamy N.R., Kondaji G. and Nagaiah K. (2002)., Bi3+ Catalyzed Regioselective ring opening of epoxides with aromatic amines., Synth. Commun., 32(15), 2307-2312.
  35. Ollevier T. and Lavie-Compin G. (2002)., An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride., Tetrahedron Lett., 43(44), 7891-7893.
  36. Paquette L.A. and Barrett J.H. (1969)., 2,7-Dimethyloxepin., Org. Synth., 49, 62.
  37. Madhukar J. and Nagavani S. (2010)., Iodine mediated mild and efficient method for the synthesis of tatrahydropyrans via cross-cyclization between epoxides and homoallylic alcohols., Orient. J. Chem., 26(3), 1151-1154.