Angularly fused triquinanes from linear substrates through trimethylenemethane diyl [2 + 3] cycloaddition reaction

Organic Letters

Volumn 12, Issue 11, 2010, Pages 2672-2674

  Lee, Hee Yoon ^a   Jung, Yongsik ^a   Yoon, Yeokwon ^a   Kim, Byung Gyu ^a   Kim, Yeonjoon ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77953014988     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100907t     Document Type: Article

References (21)

1. Yamago, S.; Nakamura, E. Org. React. 2002, 61, 1-217
2. Mehta, G. S. Chem. Rev. 1997, 97, 671-719
3. Little, R. D. Chem. Rev. 1996, 96, 93-114
4. Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563-4568
5. Lee, H. Y.; Kim, Y. J. Am. Chem. Soc. 2003, 125, 10156-10157
6. Lee, H. Y.; Kim, W. Y.; Lee, S. Tetrahedron Lett. 2007, 48, 1407-1410
7. Lee, H. Y.; Yoon, Y.; Lim, Y. H.; Lee, Y. Tetrahedron Lett. 2008, 49, 5693-5696
8. Knorr, R. Chem. Rev. 2004, 104, 3795-3849
9. Masjedizadeh, M. R.; Dannecker-Doering, I.; Little, R. D. J. Org. Chem. 1990, 55, 2742-2752
10. Starting material 4a was not completely consumed, and the yield of 5a was 45% based on the recovered starting material.
11. Siemionko, R. K.; Berson, R. A. J. Am. Chem. Soc. 1980, 102, 3870-3882
12. Examples of reactivity differences due to different substitution patterns of the olefin in the cyclopropanation reaction
13. Mori, K. Tetrahedron: Asymmetry 2007, 18, 838
14. Uchida, T.; Katsuki, T. Synthesis 2006, 1715
15. Different cycloaddition mode of Pauson-Khand reaction to form angularly fused triquinanes: Knudsen, M. J.; Schore, N. E. J. Org. Chem. 1984, 49, 5025
16. Ishizaki, M.; Iwahara, K.; Niimi, Y.; Satoh, H.; Hoshino, O. Tetrahedron 2001, 51, 2729
17. Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Lett. 1994, 35, 23-26
18. Ochiai, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281-8283
19. Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135-3142
20. Zhdankin, V. V.; Stang, P. J. Tetrahedron 1998, 54, 10927-10966
21. Ochiai, M.; Kunishima, M.; Fuji, K.; Nagao, Y. J. Org. Chem. 1988, 53, 6144-6145