Stereoselectivity in trimethylenemethane (TMM) diyl mediated cycloaddition reaction to angularly fused triquinanes

Chemistry - An Asian Journal

Volumn 6, Issue 2, 2011, Pages 646-651

  Yoon, Yeokwon ^a   Kang, Taek ^a   Lee, Hee Yoon ^a  

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

Author keywords

carbenes; cycloaddition; stereoselectivity; trimethylenemethane; triquinane

Indexed keywords

BOND INSERTION; CARBENES; CYCLOADDITION REACTION; DIASTEREO-SELECTIVITY; DIHYDROFURANS; LINEAR SUBSTRATES; TRIMETHYLENEMETHANE; TRIQUINANE;

CYCLOADDITION; ORGANIC COMPOUNDS; REACTION INTERMEDIATES;

STEREOSELECTIVITY;

EID: 79251518940     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000672     Document Type: Article

References (31)

1. P. Dowd, J. Am. Chem. Soc. 1966, 88, 2587-2589.
2. S. Yamago, E. Nakamura, Org. React. 2002, 61, 1-217.
3. G. Köbrich, H. Heinemann, J. Chem. Soc. Chem. Commun. 1969, 493-494
4. G. Köbrich, Angew. Chem. 1973, 85, 494-503
5. Angew. Chem. Int. Ed. Engl. 1973, 12, 464-473.
6. J. A. Berson, in Diradicals (Ed.:, W. T. Borden,), Wiley, New York, 1982, p. 151-194.
7. R. D. Little, M. M. Ott, Stud. Nat. Prod. Chem. 2000, 22, 195-243.
8. A. Maiti, J. B. Gerken, M. R. Masjedizadeh, Y. S. Mimieux, R. D. Little, J. Org. Chem. 2004, 69, 8574-8582.
9. B. M. Trost, J. Lynch, P. Renaud, Tetrahedron Lett. 1985, 26, 6313-6316
10. P. Binger, U. Schuchardt, Angew. Chem. 1977, 89, 254-255
11. Angew. Chem. Int. Ed. Engl. 1977, 16, 249-250.
12. B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1979, 101, 6429-6432.
13. S. Yamago, E. Nakamura, J. Am. Chem. Soc. 1989, 111, 7285-7286.
14. H. Y. Lee, Y. Kim, J. Am. Chem. Soc. 2003, 125, 10156-10157
15. H. Y. Lee, W.-Y. Kim, S. Lee, Tetrahedron Lett. 2007, 48, 1407-1410
16. H. Y. Lee, Y. Yoon, Y.-H. Lim, Y. Lee, Tetrahedron Lett. 2008, 49, 5693-5696.
17. H. Y. Lee, Y. Jung, Y. Yoon, B. G. Kim, Y. Kim, Org. Lett. 2010, 12, 2672-2675.
18. P. LeMarquand, W. Tam, Angew. Chem. 2008, 120, 2968-2970
19. Angew. Chem. Int. Ed. 2008, 47, 2926-2928
20. B. M. Trost, S. M. Silvermann, J. Am. Chem. Soc. 2010, 132, 8238-8240.
21. K. J. Stone, R. D. Little, J. Am. Chem. Soc. 1985, 107, 2495-2505.
22. G. Mehta, A. Srikrishna, Chem. Rev. 1997, 97, 671-719.
23. H. Y. Lee, H. S. Tae, B. G. Kim, H.-M. Choi, Tetrahedron Lett. 2003, 44, 5803-5806.
24. H. Fujiwara, T. Aoyama, T. Shioiri, Tetrahedron 1998, 54, 551-564.
25. C. Zanato, L. Pignataro, Z. Hao, C. Gennari, Synthesis 2008, 2158-2162.
26. J. Hibino, T. Okazone, K. Takai, H. Nozaki, Tetrahedron Lett. 1985, 26, 5579-5580.
27. R. Grigg, J. Markandu, S. Surendrakumar, M. Thornton-Prett, W. J. Warnock, Tetrahedron 1992, 48, 10399-10422.
28. G. Stork, K. Zao, Tetrahedron Lett. 1989, 30, 287-290.
29. H. Yanagisawa, K. Miura, M. Kitamura, K. Narasaka, K. Ando, Helv. Chim. Acta 2002, 85, 3130-3135
30. S. Kim, C. M. Cho, Tetrahedron Lett. 1995, 36, 4845-4848.
31. L. A. Paquette, Stud. Nat. Prod. Chem. 1993, 13, 3-52.