The dienolate [2,3]-Wittig rearrangement - Diastereoselective synthesis of highly functionalized tertiary alcohols

European Journal of Organic Chemistry

Volumn , Issue 11, 1999, Pages 2713-2724

  Hiersemann, Martin ^a   Lauterbach, Christa ^a   Pollex, Annett ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Alcohols; Aldol addition; Dienolates; 2,3 Wittig rearrangement

Indexed keywords

ALCOHOL; ESTER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032701158     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2713::aid-ejoc2713>3.0.co;2-e     Document Type: Article

References (75)

1. Undergraduate research participant September 1998.
2. [2a] J. Kallmerten in: Houben-Weyl, Methods of Organic Chemistry (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme Verlag, Stuttgart, 1995, Vol. E 21d, 3757-3809.
3. [2b] T. Nakai, K. Mikami, Org. React. 1994, 46, 105-209.
4. [2c] R. Brückner in: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Flemming, E. Winterfeldt), Pergamon Press, Oxford, 1991, Vol. 6, 873-908.
5. [2d] J. A. Marshall in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Flemming), Pergamon Press, Oxford, 1991, Vol. 3, 975-1014.
6. [2e] R. Brückner, Nachr. Chem. Tech. Lab. 1990, 38, 1506-1510.
7. [2f] K. Mikami, T. Nakai, Synthesis 1991, 594-605.
8. [2g] T. Nakai, K. Mikami, Chem. Rev. 1986, 86, 885-902.
9. For the amide enolate [2,3]-Wittig rearrangement, see: [3a] K. Mikami, O. Takahashi, T Kasuga, T. Nakai, Chem. Lett. 1985, 1729-1732.
10. [3b] M. Uchikawa, T. Hanamoto, T. Katsuki, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 4577-4580.
11. [3c] M. H. Kress, C. Yang, N. Yasuda, E. J. J. Grabowski, Tetrahedron Lett. 1997, 38, 2633-2636.
12. For the oxazoline aza-enolate [2,3]-Wittig rearrangement, see: [4a] K. Mikami, K. Fujimoto, T. Nakai, Tetrahedron Lett. 1983, 24, 513-516.
13. [4b] K. Mikami, K. Fujimoto, T. Kasuga, T. Nakai, Tetrahedron Lett. 1984, 25, 6011-6014.
14. [4c] K. Mikami, T. Kasuga, K. Fujimoto, T. Nakai, Tetrahedron Lett. 1986, 27, 4185-4188.
15. [4d] L. T. Rossano, D. J. Plata, J. Kallmerten, J. Org. Chem. 1988, 53, 5189-5191.
16. [4e] M. D. Wittman, J. Kallmerten, J. Org. Chem. 1988, 53, 4631-4633.
17. [4f] M. H. Kress, B. F. Haller, Y. Kishi, Tetrahedron Lett. 1993, 34, 8047-8050.
18. [4g] A. Sudo, Y. Hashimoto, H. Kimoto, K. Hayashi, K. Saigo, Tetrahedron: Asymmetry 1994, 5, 1333-1346.
19. [4h] X. Shi, F. X. Webster, J. Kallmerten, J. Meinwald, Tetrahedron Lett. 1995, 36, 7197-7120.
20. For the hydrazone aza-enolate [2,3]-Wittig rearrangement, see: [5a] J. L. Luengo, M. Koreeda, J. Org. Chem. 1989, 54, 5415.
21. [5b] D. Enders, D. Backhaus, J. Runsink, Angew. Chem. 1994, 106, 2167-2170; Angew. Chem. Int. Ed. Engl. 1994, 33, 2098-2100.
22. [5b] D. Enders, D. Backhaus, J. Runsink, Angew. Chem. 1994, 106, 2167-2170; Angew. Chem. Int. Ed. Engl. 1994, 33, 2098-2100.
23. [5c] D. Enders, M. Bartsch, D. Backhaus, Synlett 1995, 869-870.
24. [5d] D. Enders, D. Backhaus, J. Runsink, Tetrahedron 1996, 52, 1503-1528.
25. [5e] D. Enders, M. Bartsch, J. Runsink, Synthesis 1999, 243-248.
26. O. Takahashi, K. Mikami, T. Nakai, Chem. Lett. 1987, 69-72.
27. [7a] O. Takahashi, T. Maeda, K. Mikami, T. Nakai, Chem. Lett. 1986, 1355-1358.
28. [7b] S. Raucher, L. M. Gustavson, Tetrahedron Lett. 1986, 27, 1557-1560.
29. [7c] O. Takahashi, T. Saka, K. Mikami, T. Nakai. Chem. Lett. 1986, 1599-1602.
30. [7d] M. Uchikawa, T. Katsuki, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 4581-4582.
31. [7e] S. Kuroda. T. Katsuki, M. Yamaguchi, Tetrahedron Lett. 1987, 28, 803-804.
32. [7f] S. Kuroda, S. Sakaguchi, S. Ikegami, T. Hanamoto, T. Katsuki, M. Yamaguchi, Tetrahedron Lett. 1988, 29, 4763-4766.
33. [7g] R. Brückner, Chem. Ber. 1989, 122, 703-710.
34. [7h] K. Mikami, O. Takahashi, K. Fujimoto, T. Nakai, Synlett 1991, 629-630.
35. [7i] T. Oh, Z. Wrobel, S. M. Rubenstein Tetrahedron Lett. 1991, 32, 4647-4650. J. A. Marshall, X. Wang, J. Org. Chem. 1991, 56, 4913-4918.
36. [7i] T. Oh, Z. Wrobel, S. M. Rubenstein Tetrahedron Lett. 1991, 32, 4647-4650. J. A. Marshall, X. Wang, J. Org. Chem. 1991, 56, 4913-4918.
37. [7j] H. Okamura, S. Kuroda, S. Ikegami, K. Tomita, Y. Sugimoto, S. Sakaguchi, Y. Ito, T. Katsuki, M. Yamaguchi, Tetrahedron 1993, 49, 10531-10554.
38. [7k] K. Fujimoto, T. Nakai, Tetrahedron Lett. 1994, 35, 5019-5024.
39. [7l] M. T. Reetz, N. Griebenow, R. Goddard, J. Chem. Soc., Chem. Commun. 1995, 1605-1606.
40. [7m] T. Konno, H. Umetani, T. Kitazume, J. Org. Chem. 1997, 62, 137-150.
41. [8a] J. Martens in: Hauben-Weyl, Methods of Organic Chemistry (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme Verlag, Stuttgart, 1995, Vol. E 21d, 4199-4219.
42. For the asymmetric synthesis of 3-substituted 2-oxo esters utilizing the RAMP/SAMP method, see: [9a] D. Enders, H. Dyker, G. Raabe, J. Runsink, Synlett 1992, 901-903.
43. [9b] D. Enders, H. Dyker, G. Raabe, Angew. Chem. 1992, 104, 649-651; Angew. Chem. Int. Ed. Engl. 1992, 31, 618.
44. [9b] D. Enders, H. Dyker, G. Raabe, Angew. Chem. 1992, 104, 649-651; Angew. Chem. Int. Ed. Engl. 1992, 31, 618.
45. [9c] D. Enders, H. Dyker, F. R. Leusink, Chem. Eur. J. 1998, 4, 311-320.
46. For accounts on the chemistry of ester dienolates, see, for example: [10a] M. W. Rathke, D. Sullivan, Tetrahedron Lett. 1972, 13, 4249-4252.
47. [10b] J. L. Herrmann, G. R. Kieczykowski, R. H. Schlessinger, Tetrahedron Lett. 1973, 14, 2433-2436.
48. [10c] S. R. Wilson, R. S. Meyers, J. Org. Chem. 1975, 40, 3309-3311.
49. [10d] A. S. Kende, B. H. Toder, J. Org. Chem. 1982, 47, 163-167.
50. [10e] P. Galatsis, D. J. Parks, Tetrahedron Lett. 1994, 36, 6611-6614.
51. [10f] P. Galatsis, S. D. Millan, P. Nechala, G. Ferguson, J. Org. Chem. 1994, 59, 6643-6651.
52. [10g] E. J. Corey, B. E. Roberts, B. R. Dixon, J. Am. Chem. Soc. 1995, 117, 193-196.
53. [10h] P. Galatsis, J. J. Manwell, S. D. Millan, Tetrahedron Lett. 1996, 37, 5261-5264.
54. [10i] J. L. Garcia Ruano, I. Fernandez, M. del Prado Catalina, J. A. Hermoso, J. Sanz-Aparicio, M. Martinez-Ripoll, J. Org. Chem. 1998, 63, 7157-7161.
55. [10j] M. J. Aurell, S. Gil, R. Mestres, M. Parra, L. Parra, Tetrahedron 1998, 54, 3457-4366.
56. For an example of the oxy-Cope rearrangement of a 3-hydroxy-3-(N,N-diethylaminocarbonyl)-substituted 1,5-hexadiene, see: E. R. Koft, M. D. Williams, Tetrahedron Lett. 1986, 27, 2227-2230.
57. M. Hiersemann, Tetrahedron 1999, 55, 2625-2638.
58. [13a] G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602-625; Angew. Chem. Int. Ed. Engl. 1978, 17, 569.
59. [13a] G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602-625; Angew. Chem. Int. Ed. Engl. 1978, 17, 569.
60. [13b] B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556-557; Angew. Chem. Int. Ed. Engl. 1978, 17, 552.
61. [13b] B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556-557; Angew. Chem. Int. Ed. Engl. 1978, 17, 552.
62. An example of the chemoselective aldol addition of a 2-allyloxy-substituted ester enolate without obtaining the possible [2,3]-Wittig rearrangement product has been reported, see: Y. Nakahara, M. Shimizu, H. Yoshioka, Tetrahedron Lett. 1988, 29, 2325-2326.
63. The low diastereoselectivity of the aldol addition is a consequence of the well-known weak diastereoface-differentiating capability of (-)-menthol and/or the unselective enolization to a mixture of (E)/(Z)-configured enolates. For a review concerning cyclohexyl-based chiral auxiliaries, see: J. K. Whitesell, Chem. Rev. 1992, 92, 953-964.
64. A. M. Touzin, Tetrahedron Lett. 1975, 18, 1477-1480.
65. The terms syn and anti are utilized to assign the relative configurations based on the formulae depicted in Schemes 8 and 9. The substituted pentenoic acid is the product backbone of an enolate and dienolate [2,3]-Wittig rearrangement. For the sake of consistency with previous publications, we prefer to use the terms syn and anti based on the depicted projection.
66. M. Hiersemann, unpublished results.
67. [19a] T. Okajima, Y. Fukuzawa, Chem. Lett. 1997, 81-82.
68. The same effect was found to stabilize the calculated transition state of the [2,3]-Wittig rearrangement of a crotyloxy acetaldehyde enolate, see: [19b] K. Mikami, T. Uchida, T. Hirano, Y. Wu, K. N. Houk, Tetrahedron 1994, 50, 5917-5926.
69. It should be mentioned that we do not consider the influence of the base on the mechanism. The base should play a pivotal role with respect to the deprotonation mechanism and the fate of the protonated base. These effects can profoundly influence the course of the reaction of ester enolates; for an example, see: J. Mulzer, M. Hiersemann, J. Buschmann, P. Luger, Liebigs Ann. 1996, 649-654.
70. In a control experiment, the allyloxy-substituted ester 2b was deprotonated with LDA in THF at -78°C. The reaction mixture was stirred at -78°C for 19 h to provide only traces of the [2,3]-Wittig rearrangement product. Mainly starting material was isolated.
71. W. G. Kofron, L. M. Baclawski, J. Org. Chem. 1976, 41, 1879-1880.
72. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Peterson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzales, J. A. Pople, Gaussian 92 (Revision B.2), Gaussian, Inc., Pittsburgh PA, USA, 1995.
73. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
74. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
75. J. Reinhold, Quantentheorie der Moleküle, Teubner, Stuttgart, 1994.