New C=C bond formation via nonstoichiometric titanium(IV) halide mediated vicinal difunctionalization of α,β-unsaturated acyclic ketones

Organic Letters

Volumn 2, Issue 5, 2000, Pages 617-620

  Li, Guigen ^a   Gao, Joe ^a   Wei, Han Xun ^a   Enright, Mason ^a  

^a TEXAS TECH UNIVERSITY   (United States)

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EID: 0000378281     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9904040     Document Type: Article

References (17)

1. (a) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219.
2. (b) Brzezinski, L. J.; Rafel, S.; Leahy, J. M. J. Am. Chem. Soc. 1997, 119, 4317. For recent reviews, see:
3. (c) Ciganek, E. Org. React. 1997, 51, 201.
4. (d) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
5. During the preparation of this manuscript, a paper has appeared that mentions two examples of similar C=C formation by using different conditions (ZIE selectivity, 46/54 and 34/66; yield, 51% and 57%): Uehira, S.; Han, Z.; Shinokubo, H.; Oshima, K. Org. Lett. 1999, 1, 1383.
6. (a) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
7. (b) Xu, L.-X. Kundig, E. P. Helv. Chim. Acta 1994, 77, 1480.
8. (c) Basavaiah, D.; Hyma, R. S.; Padmaja, K.; Krishnamacharyulu, M. Tetrahedron 1999, 55, 6971 and references therein.
9. (a) Li, G.; Wei, H.-X.; Caputo, T. D. Tetrahedron Lett. 2000, 41, 1.
10. (b) Li, G.; Wei, H.-X.; Whittlesey, B.; Batrice, N. N. J. Org. Chem. 1999, 64, 1061.
11. (c) Wei, H.-X.; Hook, J. D.; Fitzgerald, K. A.; Li, G. Tetrahedron: Asymmetry 1999, 10, 661.
12. 4NI combination, see: (a) Taniguchi, M.; Hino, T.; Kishi, Y. Tetrahedron Lett. 1986, 39, 4767.
13. (b) Yachi, K.; Maeda, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5161.
14. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 139-172.
15. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986.
16. 3 solution (5 mL). The product was isolated by extraction with dichloromethane (3 × 10 mL), dried over anhydrous sodium sulfate, and concentrated to dryness. Purification by flash chromatography (EtOAc/hexane, 1/8, v/v) provided 1 (135 mg, 69%).
17. 3). 1: δ 197.3, 143.6, 136.9, 134.0, 129.8, 129.5, 128.8, 37.5, 25.8, 2: δ 197.1, 142.7, 137.1, 134.1, 129.0. 129.6, 128.8, 37.4, 25.1. 3: δ 197.1, 141.4, 138.9, 133.3, 131.1, 131.1, 130.0, 128.8, 126.8, 126.7, 126.4, 125.4, 123.9, 38.0, 26.2.4: δ 199.4, 148.0, 140.6, 139.2, 138.9, 130.1, 124, 0.37.1, 31.2, 8.2. 5: δ 196.7, 147.0, 140.3, 137.7, 134.1, 130.5, 130.2, 125.2, 37.0, 26.0. 6 δ 197.0, 141.4, 138.8, 137.6, 129.6, 125.9, 125.8, 125.8, 37.0, 25.0. 7: δ 197.3, 161.0, 143.8, 134.9, 131.9, 126.5, 114.4, 55.3, 37.9, 25.7.8: δ 196.8, 149.1, 138.2, 35.5, 31.8, 29.4, 29.4, 29.3, 29.2, 28.4, 25.4, 22.6, 14.0. 9: δ 199.2, 148.0, 140.6, 136.9, 136.8, 133.4, 131.3, 129.6, 128.6, 127.6, 124.6, 35.7, 30.6, 8.2. 10 δ 196.6, 148.1, 141.9, 137.6, 137.2, 133.5, 131.4, 129.8, 128.7, 127.6, 125.0, 35.4, 25.6.