Stereocontrolled synthesis of oxaspirobicycles via prins-pinacol annulation

Organic Letters

Volumn 11, Issue 17, 2009, Pages 3834-3837

  Chavre, Satish N ^a,b   Ullapu, Punna Reddy ^a,b   Min, Sun Joon ^a,b   Lee, Jae Kyun ^a   Pae, Ae Nim ^a,b   Kim, Youseung ^a   Cho, Yong Seo ^a,b  

^a Korea Institute of Science and Technology   (South Korea)

^b University of Science and Technology (UST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKANE; ALKENE; HETEROCYCLIC COMPOUND; OXYGEN; SPIRO COMPOUND;

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

ALCOHOLS; ALKANES; ALKENES; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; OXYGEN; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 69449101421     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9014078     Document Type: Article

References (29)

1. (a) Massias, M.; Reburrat, S.; Molho, L.; Chiaroni, A.; Riche, C.; Bodo, B. J. Am. Chem. Soc. 1990, 112, 8112.
2. (b) Abe, N.; Onoda, R.; Shirahata, K.; Kato, T.; Woods, M. C.; Kitahara, Y. Tetrahedron Lett. 1968, 9, 369.
3. (c) Misico, R. I.; Gil, R. R.; Oberti, J. C.; Veleiro, A. S.; Burton, G J. Nat. Prod. 2000, 63, 1329.
4. Pouwer, R. H.; Schill, H.; Williams, C. M.; Bernhardt, P. V. Eur. J. Org. Chem. 2007, 4699.
5. (a) Bertin, D.; Gigmes, D.; Marque, S. R. A.; Tordo, P. Tetrahedron 2005, 61, 8752.
6. (b) Nagano, H.; Ohtani, Y.; Odake, E.; Nakagawa, J.; Mori, Y.; Yajima, T. J. Chem. Res., Synop. 1999, 338.
7. Schobert, R.; Urbina-Gonzalez, J. M. Tetrahedron Lett. 2005, 46, 3657.
8. Satoh, T.; Sugiyama, S.; Kamide, Y.; Ota, H Tetrahedron 2003, 59, 4327.
9. Doyle, M. P.; Dyatkin, A. B. J. Org. Chem. 1995, 60, 3035.
10. (a) Cho, Y. S.; Karupaiyan, K.; Kang, H. J.; Pae, A. N.; Cha, J. H.; Koh, H. Y.; Chang, M. H. Chem. Commun. 2003, 2346.
11. (b) Cho, Y. S.; Kim, H. Y.; Cha, J. H.; Pae, A. N.; Koh, H. Y.; Choi, J. H.; Chang, M. H. Org. Lett. 2002, 4, 2025.
12. (c) Chavre, S. N.; Choo, H.; Cha, S. N.; Pae, A. N.; Choi, K. I.; Cho, Y. S. Org. Lett. 2006, 8, 3617.
13. (d) Ullapu, P. R.; Min, S.-J.; Charvre, S. N.; Choo, H.; Lee, J. K.; Pae, A. N.; Kim, Y.; Chang, M. H.; Cho, Y. S. Angew. Chem., Int. Ed. 2009, 48, 2196.
14. For reviews of Prins-pinacol reactions, see: (a) Overman, L. E. Aldrichim. Acta 1995, 28, 107.
15. (b) Overman, L. E. Acc. Chem. Res. 1992, 25, 352-359.
16. (c) Overman, L. E.; Pennington, L. D. J. Org. Chem. 2003, 68, 7143. For other examples, see:
17. (d) MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033.
18. (e) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overmann, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223.
19. (f) Cohen, F.; MacMillan, D. W. C.; Overman, L. E.; Romeo, A. Org. Lett. 2001, 3, 1225.
20. (g) Ponce, A. M.; Overman, L. E. J. Am. Chem. Soc. 2000, 122, 8672.
21. (h) Overman, L. E.; Velthuisen, E. J. J. Org. Chem. 2006, 71, 1581.
22. Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927.
23. Taylor, R. J. K.; Wiggins, K.; Robinson, D. H. Synthesis 1990, 589.
24. 1H NMR analysis of R-(-)- αmethoxyphenyl acetate derivatives of 6. Disappointedly, our further effort to synthesize the enantiomerically pure diol 6 has failed.
25. See the Supporting Information for details.
26. 3 position took place because the carbocation intermediate generated by acid-catalyzed ring opening is significantly stabilized by the 4-methoxyphenyl group.
27. The diol 10 was prepared following the same reaction sequences as used in Scheme 2 starting from a-hydroxymethyl cyclohexanone.
28. (a) Bal, S. A.; Marfat, A.; Helquist, P. J. Org. Chem. 1982, 47, 5045.
29. (b) Tsantali, G. G.; Takakis, I. M. J. Org. Chem. 2003, 68, 6455.