Stereoelectronic versus steric tuning in the prins cyclization reaction: Synthesis of 2fi-trans pyranyl motifs

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1741-1743

  Hu, Xu Hong ^a   Liu, Feng ^a   Loh, Teck Peng ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLENE; PYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKADIENES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PYRANS; STEREOISOMERISM;

EID: 65249114328     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900196w     Document Type: Article

References (43)

1. (a) Nicolaou. K. C; Svnder. S. A. Classics in Total Synthesis: Wilev- VCH: Weinhein, 2003. (b) Smith, A. B.; III; Fox, K. J.; Razler, T. M. Acc. Chem. Res. 2008, 41, 675-687.
2. (c) Faulkner. D. J. Nat. Prod. Rep. 2000, 17, 7-55.
3. (a) Liu, P.; Jacobsen. E. N. J Am. Chem. Soc. 2001, 123, 10772- 10773.
4. (b) Pospíšil, J.; Marko, I. E. l. Am. Chem. Soc. 2007, 129, 3516- 3517.
5. (c) Ichige, T.; Okano, Y.; Kanoh, N.; Nakata, M. J Am Chem. Soc. 2007, 129, 9862-9863.
6. (d) Su, Q.; Panek. J. S. J Am Chem. Soc. 2004, 126, 2425-2430.
7. (a) Nicolaou, K. C; Prasad, C. V. C; Somers, P. K.; Hwang, C. K. J Am Chem. Soc. 1989. 111, 5330-5334.
8. (b) Burke. S. D.; Ng, R. A.; Morrison, J. A.; Alberti, M. J. Org. Chem. 1998, 63, 3160-3161.
9. (c) Sherry. B. D.; Maus, L.; Laforteza, B. N.; Toste. F. D. J. Am. Chem. Soc. 2006,' 128, 8132-8133.
10. (d) Trost, B. M.; Yang, H.; Wuitschik, G. Qrg. Lett. 2005, 7. 4761-4764.
11. (e) Clarke, P. A.; Martin. W. H. C; Hargreaves. J. M.; Wilson, C; Blake, A. J. Chem. Commun. 2005, 1061-1063.
12. (a) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Qrg. Lett. 2002, 4, 577-580.
13. (b) Kataoka. K.; Ode. Y.; Matsumoto. M.; Nokami. J. Tetrahedron 2006, 62, 2471-2483.
14. (c) Zhang. W. C; Viswanathan, G. S.; Li. C. J. Chem. Commun. 1999, 291-292.
15. (d) Chan, K. P.; Loh, T. P. Tetrahedron Lett. 2004, 45, 8387-8390.
16. For examples, see: (a) Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Qrg. Chem. 2001, 66, 4679-4686.
17. (b) Jasti, R.; Vitale, J.; Rychnovsky, S. D. J Am Chem. Soc. 2004, 126, 9904-9905.
18. (c) Tadpetch. K.; Rychnovsky, S. D. Qrg. Lett. 2008, 10, 4839-4842.
19. (d) Evans, P. A.; Cui, J.; Gharpure, S. J. Org. Lett. 2003, 5, 3883-3885.
20. (e) Yang, X. F.; Mague, J. T.; Li, C. J. Org. Chem. 2001, 66, 739-747.
21. (f) Yadav. V. K.; Kumar. N. V. J Am Chem. Soc. 2004, 126, 8652-8653.
22. (g) Huang, H.: Panek, J. S. Qrg. Lett. 2001, 3, 1693-1696.
23. (h) Chan. K. P.; Loh. T. P. Qrg- 2005, 7, 4491-4494,
24. [4 + 2] Annulation of chiral crotvlsilanes: (a) Huang, H.; Panek, J. S. J Am. Chem. Soc. 2000, 122, 9836-9837.
25. (b) Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 3231-3234. Vinylsilane-terminated cyclizations:
26. (c) Semevn, C; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426-3427.
27. Chan. K. P.: Seow. A. H.: Loh. T. P. Tetrahedron Lett. 2007, 48, 37-41.
28. For applications of the lone pair of an ester group in the stabilization of oxo-carbenium in asymmetric synthesis, see: (a) Gung, B. W.; Xue, X.; Roush, W. R. J Am. Chem. Soc. 2002, 124, 10692-10697, and references therein,
29. (b) Loh, T. P.; Wang, R. B.; Sim, K. Y. Tetrahedron Lett. 1996, 37, 2989-2992. For a detailed study on the electrostatic attraction and anomeric effect on the stabilization of oxo-carbenium, please refer to:
30. (c) Chamberland, S.; Ziller, J. W.; Woerpel. K. A. J. Am. Chem. Soc. 2005, 127, 5322-5323.
31. (d) Ayala, L.; Lucero, C. G.; Romero, J. A. C; Tabacco. S. A.; Woerpel, K. A. J Am Chem. Soc. 2003, 125, 15521-15528, and references therein,
32. (e) Mulzer, J.: Mever. F.; Buschmann, J.; Luger, P. Tetrahedron Lett. 1995, 36, 3503-3506,
33. Preparation of allenic alcohols: (a) Lin. M. J.; Loh, T. P. J. Am. Chem. Soc. 2003, 125, 13042-13043.
34. (b) Xia, G.: Yamamoto, H. J Am. Chem. Soc. 2007, 129, 496-497.
35. (c) Yi, X. H.; Meng, Y.; Hua, X. G.; Li, C. J. Org. Chem. 1998, 63, 7472-7480.
36. (d) Nakagawa. T.; Kasatkin, A.; Sato. F. Teu-ahedron Lett. 1995, 36, 3207-3210.
37. Allenic alcohols and aldehydes could generate aldol-type adducts through 1,3-transposition of oxygen, and thus the reactions were performed at lower temperature with dropwise addition of a decreased concentration of allenic alcohols using syringe pump over a period of 1 h. For reactions of allenic alcohols and aldehydes promoted by Lewis acid, see: (a) Trost, B. M.; Jonasson, C; Wuchrer, M. J Am Chem. Soc. 2001, 123, 12736- 12737.
38. (b) Yu, C. M.; Kim, Y. M.; Kim, J. M. Synlett 2003, 1518-1520.
39. The allenic alcohol can undergo propargylic transfer in the presence of aldehyde and Lewis acid via oxo-carbenium[3,3]-sigmatropic rearrangement. Lee, K. C; Lin, M. J.: Loh, T. P. Chem. Commun. 2004, 2456- 2457.
40. For Prins cyclization of homopropargylic alcohols with aldehydes, see: (a) Miranda, P. O.; Ramírez, M. A.; Martín, V. S.; Padrón, J. I. Org. Lett. 2006, 8, 1633-1636.
41. (b) Miranda. P. O.; Díaz, D. D.; Padrón. J. L; Bermejo, J.; Martín. V. S. Qrg. Lett. 2003, 5, 1979-1982.
42. (c) Chavre, S. N.; Choo, H.; Cha, J. H.; Pae, A. N.; Choi, K. I.; Cho. Y. S. Qrg. Lett. 2006, 8, 3617-3619.
43. Roush, W. R.: Dillev. G. T. Synlett 2001, 955-959.