A tandem epoxide isomerization-aldol condensation process catalyzed by palladium acetate-tributylphosphine

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7656-7657

  Kim, Ji Hyun ^a   Kulawiec, Robert J ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000882747     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961584j     Document Type: Article

References (33)

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11. For leading examples, see: (a) Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846-5848. (b) Grigg, R.; Dorrity, M. J.; Malone, J. F.; Sridharan, V.; Sukirthalingam, S. Tetrahedron Lett. 1990, 31, 1343-1346. Zhang, Y.; Wu, G.; Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1990, 112, 8590-8592. Oppolzer, W.; De Vita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421-9438. (f) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223-269.
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13. For leading examples, see: (a) Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846-5848. (b) Grigg, R.; Dorrity, M. J.; Malone, J. F.; Sridharan, V.; Sukirthalingam, S. Tetrahedron Lett. 1990, 31, 1343-1346. Zhang, Y.; Wu, G.; Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1990, 112, 8590-8592. Oppolzer, W.; De Vita, R. J. J. Org. Chem. 1991, 56, 6256-6257. (e) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421-9438. (f) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223-269.
14. Part of this work has been communicated: Kim, J.-H.; Kulawiec, R. J. Abstracts of Papers, 210th National Meeting of the American Chemical Society, Chicago, IL; American Chemical Society: Washington, DC, 1995; ORGN 0151.
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17. 3): δ 9.66 (s, 1H), 7.44-7.15 (m, 10H), 6.87 (t, J = 7.3 Hz, 1H), 3.70 (d, J = 7.3 Hz, 2H). IR (neat): 3085, 2925, 2849, 2712, 1687, 1633, 1520, 1494, 1453, 1369, 1232.
18. (E)-2,4-Diphenyl-2-butenal was previously prepared via aldol self-condensation of phenylacetaldehyde and characterized by X-ray crystallography; see: Axelsson, O.; Becker, H. D.; Skelton, B. W.; Sørenson, H.; White, A. H. Aust. J. Chem. 1988, 41, 727-733.
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20. Product stereochemistry is assigned by analogy to compound 1, the double-bond geometry of which was determined unambiguously; see ref 9.
21. All new compounds have been fully characterized by spectroscopic techniques.
22. 3): δ 9.78 (s, 1H), 7.40-7.18 (m, 11H). 1R (neat): 3061, 2891, 2717, 1695, 1628, 1544, 1461, 1419, 1218, 1095. For a previous synthesis, see: Nerdel, F.; Weyerstahl, P.; Kühne, D.; Lengert, H.-J. Liebigs Ann. Chem. 1968, 718, 115-119.
23. See the supporting information for details of the crystallographic study. The indicated stereochemistry of the crossed-condensation products is supported by molecular mechanics calculations (MM+). In all cases, optimization using the Polak-Ribiere algorithm with a root mean square gradient of 0.4 kcal/[Å mol] gave the (E) stereoisomer as the stable configuration; see the supporting information for details.
24. For literature precedent for this mechanistic proposal, see: (a) Calhorda, M. J.; Galvão, A. M.; Ünaleroglu, C.; Zlota, A. A.; Frolow, F.; Milstein, D. Organometallics 1983, 12, 3316-3325. (b) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774 and references therein.
25. For literature precedent for this mechanistic proposal, see: (a) Calhorda, M. J.; Galvão, A. M.; Ünaleroglu, C.; Zlota, A. A.; Frolow, F.; Milstein, D. Organometallics 1983, 12, 3316-3325. (b) Milstein, D.; Calabrese, J. C. J. Am. Chem. Soc. 1982, 104, 3773-3774 and references therein.
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30. 3P=O; thus, acetate is likely to be present in our reactions.
31. (b) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605-5614.
32. 3, HOAc) do not. See the supporting information for details.
33. Nielsen A. T.; Houlihan, W. J. Org. React. 1968, 16, 1-438.