Acylation through ketene intermediates

Journal of Organic Chemistry

Volumn 67, Issue 25, 2002, Pages 8975-8982

  Shelkov, Rimma ^a   Nahmany, Moshe ^a   Melman, Artem ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVITY;

ACYLATION; ADDITION REACTIONS; ALCOHOLS; DEHYDRATION; DERIVATIVES; ESTERS;

CARBOXYLIC ACIDS;

ALCOHOL DERIVATIVE; CARBOXYLIC ACID; CYANAMIDE; DIETHYLPHOSPHONOACETIC ACID; ESTER DERIVATIVE; ETHYL 2 METHYLMALONATE; KETENE DERIVATIVE; METHYLMALONIC ACID; PHOSPHONOACETIC ACID; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CYCLOADDITION; DEHYDRATION; ESTERIFICATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037073880     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0263824     Document Type: Article

References (86)

1. (a) Macias, F. A.; Aguilar, J. M.; Molinillo, J. M. G.; Massanet, G. M.; Fronczek, F. R. Tetrahedron 1994, 50, 5439-5450.
2. (b) Kim, M. H.; Patel, D. V. Tetrahedron Lett. 1994, 35, 5603-5606.
3. (c) Baldwin, J. E.; Farthing, C. N.; Russel, A. T.; Schoffield, C. J.; Spivey, A. C. Tetrahedron Lett. 1996, 37, 3761-3764.
4. DMAP: (a) Steglich, W.; Höfle, G. Angew. Chem., Int. Ed. Engl. 1969, 8, 981.
5. (b) Review: Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
6. For the use of tributylphosphine, see: (c) Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115, 3358-3359.
7. (d) Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286-7288.
8. Esterification with DCC/DMAP: (e) Hassner, A.; Alexanian, V. Tetrahedron Lett. 1978, 4475-4478.
9. Ben, R. N.; Durstm, T. J. Org. Chem. 1999, 64, 7700-7706.
10. (a) Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto H. J. Org. Chem. 1996, 61, 4560-4567.
11. (b) Procopio, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342-2347.
12. Graham, J. M.; Shireman, B. T.; Maddux, T. M.; Brandstedt, C. M.; Zeller, W. E. Synth. Commun. 2000, 30, 1221-1226.
13. Bachi, M. D.; Korshin, E. E. Synlett 1998, 122-124.
14. Bachi, M. D.; Korshin, E. E.; Ploypradith, P.; Cumming, J. N.; Xie, S. J.; Shapiro, T. A.; Posner, G. H. Bioorg. Med. Chem. Lett. 1998, 8, 903-908.
15. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamyne, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1994, 25, 2183-2186.
16. Abnormally high rate of hydrolysis of p-nitrophenyl dimethylphosphonoacetate has been reported: Shames, S. L.; Byers, L. D. J. Am. Chem. Soc. 1981,103, 6177-6184.
17. Preliminary communication: Nahmani, M.; Melman, A. Org. Lett. 2001, 3, 3733-3735.
18. (a) Lemanski, G.; Ziegler, T. Helv. Chim. Acta 2000, 83, 2655-2675.
19. (b) Chang, H. S.; Bergmeier, S. C.; Frick, J. A.; Bathe, A.; Rapoport, H. J. Org. Chem. 1994, 59, 5336-5342.
20. (a) Ozaki, E.; Uragaki,; T, Sakashita, K.; Sakimae, A. Chem. Lett. 1995, 539-40.
21. (b) English, A. R.; Girard, D. V.; Jasys, J.; Martingano, R. J.; Kellogg, M. S. J. Med. Chem. 1990, 33, 344-347.
22. (a) Bulman Page, P. C.; Moore, J. P. G.; Mansfield, I.; McKenzie, M. J.; Bowler, W. B.; Gallagher, J. A. Tetrahedron 2001, 57, 1837-1847.
23. (b) Brooks, D. W.; Castro de Lee, N.; Peevey, R. Tetrahedron Lett. 1984, 25, 4623-4626. See also:
24. (c) Brocksom, T. J.; Petragnani, N.; Rodrigues, R. J. Org. Chem. 1974, 39, 2114-2116.
25. Review: Williams, A.; Douglas, K. T. Chem. Rev. 1975, 75, 627-649.
26. Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995.
27. (a) Allen, A. D.; Andraos, J.; Kresge, A. J.; Mcallister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 1878-1879.
28. (b) Maas, G.; Bruckmann, R. J. Org. Chem. 1985, 50, 2801-2802.
29. (c) Regitz, M.; Ruter, J. Chem. Ben 1969, 102, 3877-3890.
30. (d) Concannon, P. W.; Ciabattoni, J. J. Am. Chem. Soc. 1973, 95, 3824-3289.
31. Olah, G. A.; Wu, A. H.; Farooq, O. Synthesis 1989, 568-568.
32. Cho, B. R.; Jeong, H. C.; Seung, Y. J.; Pyun, S. Y. J. Org. Chem. 2002, 67, 5232-5238.
33. (a) Cho, B. R.; Kim, Y. K; Seung, Y. J.; Kim, J. C.; Pyun, S. Y. J. Org. Chem. 2000, 65, 1239-1242.
34. (b) Cevasco, G.; Vigo, D.; Thea, S. J. Org. Chem. 2000, 65 (23), 7833-7838.
35. (c) Inoue, M.; Bruice, T. C. J. Am. Chem. Soc. 1982, 104, 1644-1653.
36. (d) Isaac, N. S.; Najem, T. S. J. Chem. Soc., Perkin Trans. 2 1988, 557-562.
37. (e) Douglas, K. T.; Alborz, M.; Rullo, G. R.; Yaggi, N. F. J. Chem. Soc., Chem. Commun. 1982, 242-246.
38. (f) Chandrasekar, R.; Venkatasubramanian, N. J. Chem. Soc., Perkin Trans. 2 1982, 1625-1631.
39. (g) Inoue, M.; Bruice, T. C. J. Org. Chem. 1982, 47, 959-963.
40. (h) Broxton, T. J.; Duddy, N. W. J. Org. Chem. 1981, 46, 1186-1191.
41. (a) Bruice, T. C.; Holmquist, E. J. Am. Chem. Soc. 1968, 90, 7136.
42. (b) J. Am. Chem. Soc. 1969, 91, 2993.
43. DeTar, D. F.; Silverstein, R. J. Am. Chem. Soc. 1966, 88, 1013-1019.
44. Motojoshiya, J.; Hirata, K. Chem. Lett. 1988, 211-214.
45. (a) Zhou, C.; Birney, D. M. J. Am. Chem. Soc. 2002, 124, 5231-5241.
46. (b) Trahanovsky, W. S.; Surber, B. W.; Wilkes, M. C.; Preckel, M. M. J. Am. Chem. Soc. 1982, 104, 6779-6781.
47. (c) Stetter, J.; Kiehs, K. Chem. Ber. 1965, 98, 2099-2102.
48. (d) Salzner, U.; Bachrach, S. M. J. Org. Chem. 1996, 61, 237-242.
49. (e) Coleman, R. S.; Fraser; J. R. J. Org. Chem. 1993, 58, 385-392.
50. (f) Moore, H. W.; Decker, O. H. W. Chem. Rev. 1986, 86, 821-830.
51. (a) Saidi, K.; Shaterian, H.; Aghaei, D. Heterocycl. Commun. 2000, 93-95.
52. (b) Ried, W.; Nenniger, H. Synthesis 1990, 167-170.
53. (c) Yamamoto, Y.; Watanabe, Y.; Ohnishi, S. Chem. Pharm. Bull. 1987, 35, 1860-1870.
54. (d) Stetter, H.; Kiehs, K. Chem. Ber. 1965, 98, 2099-2102.
55. (e) Helv. Chim. Acta 1982, 65, 2230-2241.
56. (f) Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1987, 52, 3289-3296.
57. Ethyl malonate 1b also participates in a similar reaction.
58. For recent works involving preparation of ketenes see: (a) Allen, A. D.; Cheng, B.; Fenwick, M. H.; Huang, W. W.; Missiha, S.; Tahmassebi, D.; Tidwell, T. T. Org. Lett. 1999, 1, 693-696.
59. (b) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J.; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831-7832.
60. (c) Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J.; Lectka, T. J. Am. Chem. Soc. 2001, 123, 1531-1532.
61. (d) Bonini, B. F.; Femoni, C.; Comes-Franchini, M.; Foschi, M.; Mazzanti, G.; Ricci, A.; Varchi, G. Synlett 2001, 1092-1096.
62. Birney, D. M.; Xu, X.; Ham, S.; Huang, X. J. Org. Chem. 1997, 62, 7114-7120.
63. (a) Orlov, S. I.; Chimishkyan, A. L.; Grabarnik, M. S. Zh. Org. Khim. Engl. Trans. 1984, 19, 1977-1981.
64. (b) Hancock, C. K.; Yager, B. J.; Falls, C. P.; Schreck, J. O. J. Am. Chem. Soc. 1963, 85, 1297-1299.
65. (a) Lillford, P. J.; Satchell, D. P. N. J. Chem. Soc. B 1968, 889-897.
66. (b) Kabalina, G. A.; Askerov, D. B.; Dumaev, K. M. Zh. Org. Khim. 1982, 18, 456-457.
67. In similar competition experiments with tert-butyl alcohol the relative rates of trifluoroethanol and phenol were also less that 0.02.
68. For a review on addition reactions of ketenes see: (a) Seikali, H. R.; Tidwell, T. T. Tetrahedron 1986, 42, 2587-2613. (b) Qiao, G. G.; Andraos, J.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 5634-5638. (c) Visser, P.; Zuhse, R.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 12598-12602. (d) Wagner, B. D.; Arnold, B. R.; Brown, G. W.; Lusztyk, J. J. Am. Chem. Soc. 1998, 120, 1827-1834. (e) de Lucas, N. C.; Netto-Ferreira, J. C.; Andraos, J.; Lusztyk, J.; Wagner, B. D.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 5147-5150.
69. For a review on addition reactions of ketenes see: (a) Seikali, H. R.; Tidwell, T. T. Tetrahedron 1986, 42, 2587-2613. (b) Qiao, G. G.; Andraos, J.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 5634-5638. (c) Visser, P.; Zuhse, R.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 12598-12602. (d) Wagner, B. D.; Arnold, B. R.; Brown, G. W.; Lusztyk, J. J. Am. Chem. Soc. 1998, 120, 1827-1834. (e) de Lucas, N. C.; Netto-Ferreira, J. C.; Andraos, J.; Lusztyk, J.; Wagner, B. D.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 5147-5150.
70. For a review on addition reactions of ketenes see: (a) Seikali, H. R.; Tidwell, T. T. Tetrahedron 1986, 42, 2587-2613. (b) Qiao, G. G.; Andraos, J.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 5634-5638. (c) Visser, P.; Zuhse, R.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 12598-12602. (d) Wagner, B. D.; Arnold, B. R.; Brown, G. W.; Lusztyk, J. J. Am. Chem. Soc. 1998, 120, 1827-1834. (e) de Lucas, N. C.; Netto-Ferreira, J. C.; Andraos, J.; Lusztyk, J.; Wagner, B. D.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 5147-5150.
71. For a review on addition reactions of ketenes see: (a) Seikali, H. R.; Tidwell, T. T. Tetrahedron 1986, 42, 2587-2613. (b) Qiao, G. G.; Andraos, J.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 5634-5638. (c) Visser, P.; Zuhse, R.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 12598-12602. (d) Wagner, B. D.; Arnold, B. R.; Brown, G. W.; Lusztyk, J. J. Am. Chem. Soc. 1998, 120, 1827-1834. (e) de Lucas, N. C.; Netto-Ferreira, J. C.; Andraos, J.; Lusztyk, J.; Wagner, B. D.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 5147-5150.
72. For a review on addition reactions of ketenes see: (a) Seikali, H. R.; Tidwell, T. T. Tetrahedron 1986, 42, 2587-2613. (b) Qiao, G. G.; Andraos, J.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 5634-5638. (c) Visser, P.; Zuhse, R.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 12598-12602. (d) Wagner, B. D.; Arnold, B. R.; Brown, G. W.; Lusztyk, J. J. Am. Chem. Soc. 1998, 120, 1827-1834. (e) de Lucas, N. C.; Netto-Ferreira, J. C.; Andraos, J.; Lusztyk, J.; Wagner, B. D.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 5147-5150.
73. (a) Lillford, P. J.; Satchell, D. P. N. J. Chem. Soc. B 1968, 889-897.
74. (b) Nguyen, M. T.; Hegarty, A. F. J. Am. Chem. Soc. 1984, 106, 1551-1557.
75. (a) Allen, A. D.; Andraos, J.; Kresge, A. J.; Mcallister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 1878-1879.
76. (b) Urlwyler, B.; Wirz, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 790-791.
77. (a) Chiang, Y.; Guo, H.-X.; Kresge, A. J.; Tee, O. S. J. Am. Chem. Soc. 1996, 118, 3386-3391.
78. (b) Chiang, Y.; Kresge, A. J.; Meng, Q.; Morita, Y.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 8345-8351.
79. (a) Meyer, H.; Wengenroth, H.; Lauer, W. Chem. Ber. 1988, 121, 1643-1646.
80. (b) Meyer, H.; Wengenroth, H.; Lauer, W.; Krause, V. Tetrahedron Lett. 1983, 24, 5525-5526.
81. Molecular orbital calculations: (c) Allen, A. D.; McAllister, M. A.; Tidwell, T. T. Tetrahedron Lett. 1993, 34, 1095-1098.
82. (d) Birney, D. M.; Wagenseller, P. E. J. Am. Chem. Soc. 1994, 116, 6262-6270.
83. (e) Shumway, W. W.; Dalley, N. K.; Birney, D. M. J. Org. Chem. 2001, 66, 5832-5839.
84. (f) Shumway, W.; Ham, S.; Moer, J.; Whittlesey, B. R.; Birney, D. M. J. Org. Chem. 2000, 65, 7731-7739.
85. Tidwell, T. T. Acc. Chem. Res. 1990, 23, 273-279.
86. Allen, A. D.; Stevenson, A.; Tidwell, T. T. J. Org. Chem. 1989, 54, 2843, 2848.