[3 + 4] Annulation of α,β-unsaturated acylsilanes with enolates of α,β-unsaturated methyl ketones: Scope and mechanism

Journal of the American Chemical Society

Volumn 120, Issue 20, 1998, Pages 4947-4959

  Takeda, Kei ^a   Nakajima, Akemi ^a   Takeda, Mika ^a   Okamoto, Yasushi ^a   Sato, Taku ^a   Yoshii, Eiichi ^a   Koizumi, Toru ^a   Shiro, Motoo ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; ISOMERISM; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032572060     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980022+     Document Type: Article

References (47)

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2. For general reviews, see: (a) Ho, T.-L. Carbocycle Construction in Terpene Synthesis; VCH: New York, 1988. (b) Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley & Sons: New York, 1983; Vol. 5, pp 333-390.
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24. For reviews on acylsilanes, see: (a) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (b) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (c) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (d) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660.
25. For reviews on acylsilanes, see: (a) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (b) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (c) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (d) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660.
26. For reviews on acylsilanes, see: (a) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (b) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (c) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (d) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660.
27. Reuss, R. H.; Hassner, A. J. Org. Chem. 1974, 39, 1785-1787.
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29. Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans, 1 1995, 317-337.
30. For reviews on rearrangement of divinylcyclopropanes, see ref 2b. See also: (a) Piers, E. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 971-998. (b) Hill, R. K. Ibid.; Vol. 5, pp 785-826.
31. For reviews on rearrangement of divinylcyclopropanes, see ref 2b. See also: (a) Piers, E. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 971-998. (b) Hill, R. K. Ibid.; Vol. 5, pp 785-826.
32. (a) Wilson, S. R. Org. React. 1993, 43, 93-250.
33. For related charge accelerated rearrangements, see: (b) Bronson, J. J.; Danheiser, R. L. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 999-1036.
34. For thermal Cope rearrangement of cis-1-aryl-2-vinylcyclopropanes, see: Marvell, E. N.; Lin, C. J. Am. Chem. Soc. 1978, 100, 877-883. See also ref 11b.
35. Takeda, K.; Nakatani, J.; Nakamura, H.; Sako, K.; Yoshii, E.; Yamaguchi, K. Synlett 1993, 841-843.
36. Takeda, K.; Sakurama, K.; Yoshii, E. Tetrahedron Lett. 1997, 38, 3257-3260.
37. This compound was prepared according to Wulff's procedure. Murray, C. K.; Yang, D. C.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 5660-5662.
38. Similar results have been reported for the reaction of Danishefsky's diene and cyclohexenylmethoxychromium carbene complex by Wulff and co-workers. Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J.; Miller, R. A.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642-3659. The relatively facile cis-to-trans isomerization of 41 involving ring-opening/reclosure and the fast thermal Cope rearrangement of the cis derivative of 41 may be interpreted in terms of the push-pull effect by the siloxy and acetoxy groups.
39. For an oxyanion-accelerated vinylcyclopropane rearrangement, see: (a) Danheiser, R. L.; Martinez-Davila, C.; Morin, J. M., Jr. J. Org. Chem 1980 45 1340-1341. (b) Danheiser, R. L.; Martinez-Davila, C.; Auchus, R. J.; Kadonaga, J. T. J. Am. Chem. Soc. 1981, 103, 2443-2446. See also ref 12b.
40. For an oxyanion-accelerated vinylcyclopropane rearrangement, see: (a) Danheiser, R. L.; Martinez-Davila, C.; Morin, J. M., Jr. J. Org. Chem 1980 45 1340-1341. (b) Danheiser, R. L.; Martinez-Davila, C.; Auchus, R. J.; Kadonaga, J. T. J. Am. Chem. Soc. 1981, 103, 2443-2446. See also ref 12b.
41. The major side product of the reaction was bicyclo[4.1.0]heptene i (X-ray) which was an intramolecular C-H insertion product of Diels-Alder adduct ii. (Matrix Presented) See: Takeda, K.; Okamoto, Y.; Nakajima, A.; Yoshii, E.; Koizumi, T. Synlett 1997, 1181-1183.
42. We believe that the slower trans-to-cis isomerization of 51 relative to more congested 41 would be due to the lower ground-state energy of the trans-1,2-divinylcyclopropropanolate from 51 than that of 41.
43. We will report the mechanistic details of the [3 + 2] annulation including the comparison of α-carbanion-stabilizing ability between the phenylthio and trimethylsilyl groups elsewhere.
44. Takeda, K,; Okamoto, Y.; Koizumi, T. Unpublished results. Also, see ref 19.
45. Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798-2802.
46. Reaction with crotonoylsilane 70 (R = Me) gave a poor yield of the cycloheptenone presumably because of decomposition caused by enolate-mediated deprotonation of the β-methyl group of 70.
47. Ager, D. J.; Fleming, I.; Patel, S. K. J. Chem. Soc., Perkin Trans. 1 1981, 2520-2526.