8-Endo selective Friedel-Crafts cyclization of vinyloxiranes with Co2(CO)6-complexed acetylene

Tetrahedron Letters

Volumn 50, Issue 1, 2009, Pages 26-28

  Nagumo, Shinji ^a   Ishii, Yusuke ^b   Sato, Gen ^b   Mizukami, Megumi ^b   Imai, Masanori ^b   Kawahara, Norio ^b   Akita, Hiroyuki ^c  

^a KOGAKUIN UNIVERSITY   (Japan)

^b HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

^c TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; ACETYLENE; BENZENEACETYLENE; CARBON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; FRIEDEL CRAFTS REACTION; STEREOCHEMISTRY;

EID: 56949097429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.043     Document Type: Article

References (27)

1. Nagumo S., Miyoshi I., Akita H., and Kawahara N. Tetrahedron Lett. 43 (2002) 2223
2. Nagumo S., Mizukami M., Wada K., Miura T., Bando H., Kawahara N., Hashimoto Y., Miyashita M., and Akita H. Tetrahedron Lett. 48 (2007) 8558
3. Mizukami M., Saito H., Higuchi T., Imai M., Bando H., Kawahara N., and Nagumo S. Tetrahedron Lett. 48 (2007) 7228
4. For representative examples:. Jamison T.F., Shambayati S., Crowe W.E., and Schreiber S.L. J. Am. Chem. Soc. 119 (1997) 4353
5. Iwasawa N., and Satoh H. J. Am. Chem. Soc. 121 (1999) 7951
6. Takai S., and Isobe M. Org. Lett. 4 (2002) 1183
7. Tanino K., Kondo F., Shimizu T., and Miyashita M. Org. Lett. 4 (2002) 2217
8. Kira K., Hamajima A., and Isobe M. Tetrahedron 58 (2002) 1875
9. Teobald B.J. Tetrahedron 58 (2002) 4133
10. Tanino K., Onuki K., Asano K., Miyashita M., Nakamura T., Takahashi Y., and Kuwajima I. J. Am. Chem. Soc. 125 (2003) 1498
11. Young D.G.J., Burlison J.A., and Peters J. J. Org. Chem. 68 (2003) 3494
12. Baba T., Takai S., Sawada N., and Isobe M. Synlett (2004) 603
13. Ortega N., Martin T., and Martin V.S. Org. Lett. 8 (2006) 871
14. DiMartino J., and Green J.R. Tetrahedron 62 (2006) 1402
15. Inaba K., Takaya J., and Iwasawa N. Chem. Lett. 36 (2007) 474 references cited therein
16. See also:. Yet L. Chem. Rev. 100 (2000) 2963
17. Nagasawa T., Kitamura M., and Suzuki K. Synlett (1995) 1183
18. Kitamura M., Ohmori K., and Suzuki K. Tetrahedron Lett. 40 (1999) 4563
19. 6-complexed eneyne, see also:. Mikami K., Feng F., Matsueda H., Yoshida A., and Grierson D.S. Synlett (1996) 833
20. 3) δ 167.30 (s), 158.84 (s), 158.18 (s), 151.59 (d), 139.45 (s), 134.53 (d), 126.84 (d), 121.61 (d), 119.26 (s), 105.02 (d), 98.23 (d), 69.63 (d), 55.39 (q), 55.18 (q), 51.24 (q), 48.10 (d), 29.09 (t), 24.80 (t).
21. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 50 (1975) 4467
22. The meta methoxy group to the reacting site generally exerts an electron-withdrawing inductive effect. It was thus interesting that the cyclization of 8d proceeded smoothly in spite of the presence of the methoxy group at the C4′ position. A previously reported 7-endo cyclization of 3′,4′-dimethoxyphenylpropyl vinyloxirane (see Ref. 1) can be explained to proceed via an ipso-cyclization and the subsequent migration. Such a mechanism might be inadequate in the case of 8d because the neighbouring effect of the cobalt complex might inhibit an ipso-cyclization.
23. These vinyloxiranes were prepared as optically active compounds.
24. A previously reported 7-endo cyclization of 3′-methoxyphenylpropyl vinyloxirane having no adjacent ester group yielded a mixture of stereoisomers (see Ref. 1). However, the corresponding vinyloxirane having an adjacent ester group proceeded stereospecifically to give only trans-isomer.
25. Unpublished data.
26. Tanino K., Shimizu T., Miyashita M., and Kuwajima I. J. Am. Chem. Soc. 122 (2000) 6116
27. Hosokawa S., and Isobe M. Tetrahedron Lett. 39 (1998) 2609