Enantioselective allylic substitution using a novel (phosphino-1,3-oxazine)palladium catalyst

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9143-9146

  Evans, P Andrew ^a   Brandt, Thomas A ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CHALCONE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COVALENT BOND; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030590966     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02162-4     Document Type: Article

References (26)

1. 1. Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993.
2. 2. For reviews on asymmetric allylic alkylation, see: (a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
3. (b) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
4. (c) Hayashi, T. in Catalytic Asymmetric Synthesis; Ojima, I. Ed; VCH Publishers: New York, 1993, p 325.
5. (d) Trost, B. M.; Van Vranken, D. L. Chem Rev. 1996, 96, 395.
6. 3. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1992, 114, 9327.
7. (b) Trost, B. M.; Breit, B.; Organ, M. G. Tetrahedron Lett. 1994, 35, 5817.
8. (c) Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520 and pertinent references cited therein.
9. 4. (a) Auburn, P. R.; MacKenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033.
10. (b) Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191.
11. (c) von Matt, P.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 566.
12. (d) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769.
13. (e) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149.
14. (f) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135.
15. (g) Brenchley, G.; Merifield, E.; Wills, M.; Fedouloff, M. Tetrahedron Lett. 1994, 35, 2791.
16. (h) Tanner, D.; Andersson, P. G.; Harden, A.; Somfai, P. Tetrahedron Lett. 1994, 35, 4631.
17. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493.
18. (j) Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kuhnle, F. N. M.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta 1995, 78, 1636.
19. (k) Yamazaki, A.; Achiwa, K. Tetrahedron Asymmetry 1995, 6, 51.
20. (l) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657.
21. (m) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
22. (n) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545.
23. (o) Zhu, G.; Terry, M.; Zhang, X. Tetrahedron Lett. 1996, 37, 4475 and pertinent references cited within these articles.
24. 5. Evans, P. A.; Brandt, T. A.; Nelson, J. D. Manuscript in preparation.
25. 4, filtered and concentrated in vacuo to afford a crude oil. Purification by flash chromatography (eluting with 7-20% gradient of ethyl acetate/hexane) gave the allylic alkylation product 2 (0.169 g, 99%) as a colorless oil.
26. 7. Spritz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523 and pertinent references cited therein.