Asymmetric iodolactonization utilizing chiral squaramides

Organic Letters

Volumn 14, Issue 23, 2012, Pages 5884-5887

  Tungen, Jorn E ^a   Nolsoe, Jens M J ^a   Hansen, Trond V ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; CYCLOBUTANE DERIVATIVE; GAMMA BUTYROLACTONE; IODINATED HYDROCARBON; SQUARIC ACID;

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

4-BUTYROLACTONE; CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; CYCLOBUTANES; HYDROCARBONS, IODINATED; HYDROGEN BONDING; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84870947821     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302798g     Document Type: Article

References (54)

1. Snyder, S. A.; Treitler, D. S.; Brucks, A. P. Aldrichimica Acta 2011, 44, 27
2. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Synlett 2011, 1335
3. Ranganathan, S.; Muraleedharan, K. M.; Vaish, N. K.; Jayaraman, N. Tetrahedron 2004, 60, 5273
4. Dowle, M. D.; Davies, D. I. Chem. Soc. Rev. 1979, 8, 171
5. Woodward, R. B.; Singh, G. J. Am. Chem. Soc. 1950, 72, 5351
6. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675
7. Danishefsky, S.; Schuda, P. F.; Kitahara, T.; Etheredge, S. J. J. Am. Chem. Soc. 1977, 99, 6066
8. Zhou, Q.; Snider, B. B. Org. Lett. 2008, 10, 1401
9. Laya, M. S.; Banerjee, A. K.; Cabrera, E. V. Curr. Org. Chem. 2009, 13, 720
10. French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354
11. Vik, A.; Hansen, T. V. Tetrahedron Lett. 2011, 52, 1060
12. Vik, A.; Hansen, T. V.; Holmeide, A. K.; Skattebol, L. Tetrahedron Lett. 2010, 51, 2852
13. Langseter, A. M.; Skattebol, L.; Stenstrom, Y. Tetrahedron Lett. 2012, 53, 940
14. Holmeide, A. K.; Skattebol, L.; Sydnes, M. J. Chem. Soc., Perkin Trans. 1 2001, 1942
15. Stivala, C. E.; Gu, Z.; Smith, L. L.; Zakarian, A. Org. Lett. 2012, 14, 804
16. Canham, S. M.; France, D. J.; Overman, L. E. J. Org. Chem. 2012, 10.1021/jo300872y
17. Snyder, S. A.; Wright, N. E.; Pflueger, J. J.; Breazzano, S. P. Angew. Chem., Int. Ed. 2011, 50, 8629
18. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291
19. Hart, D. J.; Huang, H.-C.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507
20. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175
21. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728
22. Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett. 1999, 40, 8827
23. Kitagawa, O.; Hanano, T.; Tanabe, K.; Shiro, M.; Taguchi, T. J. Chem. Soc., Chem. Commun. 1992, 1005
24. Grossman, R. B.; Trupp, R. J. Can. J. Chem. 1998, 76, 1233
25. Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297
26. Haas, J.; Bissmire, S.; Wirth, T. Chem.î-̧Eur. J. 2005, 11, 5777
27. Garnier, J. M.; Robin, S.; Rousseau, G. Eur. J. Org. Chem. 2007, 3281
28. Whitehead, D. C.; Yousefi, R.; Jaganathan, A.; Borhan, B. J. Am. Chem. Soc. 2010, 132, 3298
29. Yousefi, R.; Whitehead, D. C.; Mueller, J. M.; Staples, R. J.; Borhan, B. Org. Lett. 2011, 13, 608
30. Zhang, W.; Zheng, S.; Liu, N.; Werness, J. B.; Guzei, I. A.; Tang, W. J. Am. Chem. Soc. 2010, 132, 3664
31. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474
32. Murai, K.; Matsushita, T.; Nakamura, A.; Fukushima, S.; Shimura, M.; Fujioka, H. Angew. Chem., Int. Ed. 2010, 49, 9174
33. Wang, M.; Gao, L. X.; Wen, P. M.; Xia, A. X.; Wang, F.; Zhang, S. B. J. Org. Chem. 2004, 69, 2874
34. Ning, Z. L.; Jin, R. H.; Ding, J. Y.; Gao, L. X. Synlett 2009, 2291
35. Veitch, G. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 7332
36. Ning, Z.-L.; Ding, J.-Y.; Jin, R.-Z.; Kang, C.-Q.; Cheng, Y.-Q.; Gao, L.-X. Chem. Res. Chin. Univ. 2011, 27, 45
37. During our investigations and preparation of this manuscript a highly enantioselective protocol for iodolactonization was disclosed, utilizing Bronsted acid catalysis: Dobish, M. C.; Johnston, J. N. J. Am. Chem. Soc. 2012, 134, 6068
38. Pihko, P. M. Hydrogen bonding in Organic Synthesis; Wiley-VCH: 2009.
39. Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713
40. Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062
41. Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289
42. Malerich, J. P.; Hagihara, K.; Rawal, V. H. J. Am. Chem. Soc. 2008, 130, 14416
43. Review of squaramides as organocatalysts: Alemán, J.; Parra, A.; Jiang, H.; Jorgensen, K. A. Chem.î-̧Eur. J. 2011, 17, 6890
44. Noole, A.; Järving, I.; Werner, F.; Lopp, M.; Malkov, A.; Kanger, T. Org. Lett. 2012, 14, 4922
45. Sun, W.; Zhu, G.; Wu, C.; Hong, L.; Wang, R. Chem.î-̧Eur. J. 2012, 18, 6737
46. Albrecht, A.; Dickmeiss, G.; Acosta, F. C.; Rodríguez-Escrich, C.; Davis, R. L.; Jorgensen, K. A. J. Am. Chem. Soc. 2012, 134, 2543
47. Ling, J.-B.; Su, Y.; Zhu, H.-L.; Wang, G.-Y.; Xu, P.-F. Org. Lett. 2012, 14, 1090
48. Yang, H.-J.; Dai, L.; Yang, S.-Q.; Chen, F.-E. Synlett 2012, 23, 948
49. Dai, L.; Yang, H.; Niu, J.; Chen, F.-E. Synlett 2012, 23, 314
50. Chaikovskii, V. K.; Funk, A. A.; Filiminov, V. D.; Petrenko, T. V.; Kets, T. S. Russ. J. Org. Chem. 2008, 44, 935
51. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734
52. Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, 111, 6513
53. Johnson, C. D. Acc. Chem. Res. 1993, 26, 476
54. Baldwin, J. E.; Thomas, R. C.; Kruse, L. I.; Silberman, L. J. Org. Chem. 1977, 42, 3846