Z-selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocyclic alkenes

Tetrahedron Letters

Volumn 52, Issue 12, 2011, Pages 1284-1287

  Ando, Kaori ^a   Sato, Kaori ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; MACROCYCLIC COMPOUND; SODIUM DERIVATIVE; SODIUM HYDRIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DILUTION; HORNER WADSWORTH EMMONS REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 79951730434     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.043     Document Type: Article

References (31)

1. For a review: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
2. (a) Stork, G.; Nakamura, E. J. Org. Chem. 1979, 44, 4010-4011;
3. (b) Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R.; Petasis, N. A. J. Org. Chem. 1979, 44, 4011-4013.
4. Ando, K.; Narumiya, K.; Takada, H.; Teruya, T. Org. Lett. 2010, 12, 1460-1463.
5. For Z-selective HWE reactions: (a) Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408;
6. (b) Ando, K. Tetrahedron Lett. 1995, 36, 4105-4108;
7. (c) Ando, K. J. Org. Chem. 1997, 62, 1934-1939;
8. (d) Ando, K. J. Org. Chem. 1998, 63, 8411-8416;
9. (e) Ando, K. J. Org. Chem. 1999, 64, 8406-8408;
10. (f) Ando, K.; Oishi, T.; Hirama, M.; Ohno, H.; Ibuka, T. J. Org. Chem. 2000, 65, 4745-4749;
11. (g) Ando, K. J. Synth. Org. Chem. Jpn. 2000, 58, 869-876.
12. (a) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035-1039;
13. (b) Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 6389-6391;
14. (c) Stocksdale, M. G.; Ramurthy, S.; Miller, M. J. J. Org. Chem. 1998, 63, 1221-1225;
15. (d) Yao, H.; Gao, Y.; Liu, P.; Sun, B.; Xu, X. Synlett 2007, 571-574.
16. (a) Marshall, J. A.; DeHoff, B. S. Tetrahedron Lett. 1986, 27, 4873-4876;
17. (b) Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849-4860;
18. (c) Kodama, M.; Shiobara, Y.; Sumitomo, H.; Fukuzumi, K.; Minami, H.; Miyamoto, Y. Tetrahedron Lett. 1986, 27, 2157-2160;
19. (d) Zhang, J.; Xu, X. Tetrahedron Lett. 2000, 41, 941-943.
20. (a) Marshall, J. A.; DeHoff, B. S.; Cleary, D. G. J. Org. Chem. 1986, 51, 1735-1741;
21. (b) Medina, J. C.; Guajardo, R.; Kyler, K. S. J. Am. Chem. Soc. 1989, 111, 2310-2311;
22. (c) Hammond, G. B.; Cox, M. B.; Wiemer, D. F. J. Org. Chem. 1990, 55, 128-132;
23. (d) Noguchi, H.; Aoyama, T.; Shioiri, T. Tetrahedron 1995, 51, 10545-10560.
24. Yoshida, Y.; Sakakura, Y.; Aso, N.; Okada, S.; Tanabe, Y. Tetrahedron 1999, 55, 2183.
25. Touchard, F. P.; Capelle, N.; Mercier, M. Adv. Synth. Catal. 2005, 347, 707-711.
26. 1H NMR, 13 was isolated by flash chromatography (hexane/AcOEt = 30:1) as a colorless oil (0.036 g, 63% yield) (Z:E = 97:3).
27. 1H NMR spectra and mass spectroscopy.
28. 2, see: (a) Ando, K.; Nagaya, S.; Tarumi, Y. Tetrahedron Lett. 2009, 50, 5689-5691;
29. For the polymer-supported reagents, see: (b) Ando, K.; Suzuki, Y. Tetrahedron Lett. 2010, 51, 2323-2325.
30. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
31. For a computational investigation of the reaction mechanism, see: Ando, K. J. Org. Chem. 1999, 64, 6815-6821.