Highly Z-selective synthesis of a,b-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction

Tetrahedron Letters

Volumn 54, Issue 15, 2013, Pages 2026-2028

  Ando, Kaori ^a   Okumura, Miho ^a   Nagaya, Shigeo ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

A,b Unsaturated nitriles; Aldehydes; Stereoselectivity; The HWE reaction; Z Selective

Indexed keywords

ALDEHYDE; ALKENE; ALPHA,BETA UNSATURATED NITRILE; NITRILE; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; HORNER WADSWORTH EMMONS REACTION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 84874950856     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.020     Document Type: Article

References (33)

1. Ando, K. Tetrahedron Lett. 1995, 36, 4105-4108.
2. Ando, K. J. Org. Chem. 1997, 62, 1934-1939.
3. Ando, K. J. Org. Chem. 1998, 63, 8411-8416.
4. Ando, K. J. Org. Chem. 1999, 64, 8406-8408.
5. Ando, K.; Oishi, T.; Hirama, M.; Ohno, H.; Ibuka, T. J. Org. Chem. 2000, 65, 4745-4749.
6. For a computational investigation of the reaction mechanism, see: Ando, K. J. Org. Chem. 1999, 64, 6815-6821.
7. For reviews: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
8. Ando, K. J. Synth. Org. Chem. Jpn. 2000, 58, 869-876.
9. Ando, K. unpublished results.
10. Zhang, T. Y.; O. Toole, J. C.; Dunigan, J. M. Tetrahedron Lett. 1998, 39, 1461-1464. The 12:1 Selectivity was reported for the reaction with a long chain dialdehyde,
11. Stockman, R. A.; Sinclair, A.; Arini, L. G.; Szeto, P.; Hughes, D. L. J. Org. Chem. 2004, 69, 1598-1602.
12. Kojima, S.; Fukuzaki, T.; Yamakawa, A.; Murai, Y. Org. Lett. 2004, 6, 3917-3920.
13. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-5570.
14. Haruta, R.; Ishiguro, M.; Furuta, K.; Mori, A.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1093-1096.
15. Fang, F.; Li, Y.; Tian, S.-K. Eur. J. Org. Chem. 2011, 1084-1091.
16. Kojima, S.; Kawaguchi, K.; Matsukawa, S.; Uchida, K.; Akiba, K. Chem. Lett. 2002, 170-171.
17. Tomioka, T.; Takahashi, Y.; Vaughan, T. G.; Yanase, T. Org. Lett. 2010, 12, 2171-2173.
18. Yazaki, R.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 3195-3197.
19. Sato, Y.; Niinomi, Y. J. Chem. Soc., Chem. Commun. 1982, 56-57.
20. Touchard, F. P.; Capelle, N.; Mercier, M. Adv. Synth. Catal. 2005, 347, 707-711.
21. For the amide reagents, (o-tBuC6H4O)2P(O)CH2CONR1R2, see: (a) Ando, K.; Nagaya, S.; Tarumi, Y. Tetrahedron Lett. 2009, 50, 5689-5691.
22. For the polymersupported reagents, see: (b) Ando, K.; Suzuki, Y. Tetrahedron Lett. 2010, 51, 2323-2325.
23. For the intramolecular HWE reagents, see: (c) Ando, K.; Narumiya, K.; Takada, H.; Teruya, T. Org. Lett. 2010, 12, 1460-1463.
24. Ando, K.; Sato, K. Tetrahedron Lett. 2011, 52, 1284-1287.
25. The E:Z ratios were determined by integration of the vinyl proton signals in 400 MHz 1H NMR spectra of the crude reaction mixture. All the HWE products described in this Letter except for 5j are known compounds. 1H NMR spectra are identical to the reported values: Z-5a,6a E-5a,13a Z-5b,8a E-5b,13a Z-5c,6a E-5c,13a Z-5d,6a E-5d,13a Z-5e,13b E-5e,13c Z-5f,7a E-5f,7a Z-5g,7a E-5g,13a Z-5h,6a E-5h,6a Z-5k,6a E-5k,6a Z-5l,13d E-5l,13d Z-5m,6a E-5m,6a Z-5n,8a E-5n,8a Z-5o,6a E-5o,6a Z-6,13e E-6.13f The NMR spectrum of 5i was not reported.4 Both 5i and 5j were characterized by 400 MHz 1H NMR spectra, mass spectroscopy, and HRMS.
26. A typical procedure for the Z-selective HWE reaction (entry 8 in Table 2): A solution of 2e (0.30 mmol) and 18-crown-6 (0.105 g, 0.39 mmol) in THF (6 mL) was treated with t-BuOK (0.045 g, 0.39 mmol) at 0 -C. 15 min later, the mixture was cooled to -78 -C and o-methylbenzaldehyde (0.039 mL, 0.33 mmol) was added. The resulting mixture was stirred at -78 -C for 2.5 h. The reaction was quenched with aqueous NH4Cl, and the mixture was extracted with AcOEt twice (7 and 4 mL). The combined extracts were washed with brine, dried (MgSO4), and concentrated. After determining the Z/E ratio (>99:1) of the crude mixture by 400 MHz 1H NMR, the olefin was isolated by flash chromatography (hexane:AcOEt = 20:1) as a colorless oil (0.039 g, 90% yield) (Z/E = >99:1).
27. Qin, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 15893-15895.
28. Senra, J. D.; Malta, L. F. B.; Souza, A. L. F.; Aguiar, L. C. S.; Antunes, O. A. C. Adv. Synth. Catal. 2008, 350, 2551-2558.
29. Shaaban, M. R.; Darweesh, A. F.; Dawood, K. M.; Farag, A. M. ARKIVOC 2010, 208-225.
30. Grée, D.; Vallerie, L.; Grée, R.; Toupet, L.; Washington, I.; Pelicier, J.-P.; Villacampa, M.; Pérez, J. M.; Houk, K. N. J. Org. Chem. 2001, 66, 2374-2381.
31. Oyamada, J.; Kitamura, T. Chem. Commun. 2008, 4992-4994.
32. Ren, G.; Cui, X.; Yang, E.; Yang, F.; Wu, Y. Tetrahedron 2010, 66, 4022-4028.
33. Pihko, P. M.; Salo, T. M. Tetrehedron Lett. 2003, 44, 4361-4364.