Intramolecular [3 + 2]cycloaddition reaction of dipolar trimethylenemethane

Chemistry Letters

Volumn , Issue 6, 2000, Pages 664-665

  Nakamura, Masaharu ^b   Toganoh, Motoki ^b   Wang, Xio Qun ^b   Yamago, Shigeru ^a   Nakamura, Eiichi ^b  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034354514     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.664     Document Type: Article

References (17)

1. D. F. Taber, "Intramolecular Diels-Alder and Alder Ene Reations," Springer-Verlag, New York (1984).
2. a) S. Yamago and E. Nakamura, J. Am. Chem. Soc., 111, 7285 (1989).
3. b) S. Yamago and E. Nakamura, J. Org. Chem., 55, 5553 (1990).
4. c) E. Nakamura, S. Yamago, S. Ejiri, A. E. Dorigo, and K. Morokuma, J. Am. Chem. Soc., 113, 3183 (1991).
5. d) S. Ejiri, S. Yamago, and E. Nakamura, J. Am. Chem. Soc., 114, 8707 (1992).
6. e) S. Yamago, S. Ejiri, M. Nakamura, and E. Nakamura, J. Am. Chem. Soc., 115, 5344 (1993).
7. f) S. Yamago, S. Ejiri, and E. Nakamura, Angew. Chem., Int. Ed. Engl., 34, 2154 (1995).
8. g) S. Yamago, M. Nakamura, X. Q. Wang, M. Yanagawa, S. Tokumitsu, and E. Nakamura, J. Org. Chem., 63, 1694 (1998).
9. h) S. Yamago, M. Yanagawa, and E. Nakamura, Chem. Lett., 1999, 879.
10. i) M. Nakamura, M. Toganoh, H. Ohara, and E. Nakamura, Org. Lett., 1, 7 (1999).
11. R. D. Little, Chem. Rev., 96, 93 (1996).
12. M. Isaka, S. Ejiri, and E. Nakamura, Tetrahedron, 48, 2045 (1992).
13. The product was a mixture of stereoisomers (E:Z = 79:21-81:11). This mixture could be partially separated by flash column chromatography.
14. Hb-Hc = 6.0 Hz for 8b. cf. B. M. Trost, T. A. Grese, and D. M. T. Chan, J. Am. Chem. Soc., 113, 7350 (1991).
15. +: 313.2015.
16. B. M. Trost and I. Fleming, "Comprehensive Organic Synthesis," Pergamon, Oxford (1991), Vol. 4, pp. 513-550.
17. The structure of the cis-fused isomer of 9b was determined previously by X-ray crystallographic analysis: T. Yamada, H. Uekusa, Y. Ohashi, S. Yamago, X. Q. Wang, and E. Nakamura, Acta Cryst., C51, 1137 (1995). Interestingly, upon exposure to silica gel, the trans-fused isomer of 9b underwent hydrolysis of the C-C single bond between the acetal carbon and carbon connected to the two ester groups. This observation suggests us that the cis-fused [3.3.0] system is highly strained.