A Novel [3 + 2] Annelation between ortho-Carboranyltrimethylsilane and Conjugated Carbonyl Compounds

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 4, 1997, Pages 367-369

  Nakamura, Hiroyuki ^b   Aoyagi, Kouichi ^a   Singaram, Bakthan ^c   Cai, Jianping ^d   Nemoto, Hisao ^d   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

Aldehydes; Annulation; Carboranes; Ketones

Indexed keywords

EID: 0030948010     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199703671     Document Type: Article

References (25)

1. Reviews: Comprehensive Organic Synthesis, Vol. 5 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, pp. 240-314.
2. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
3. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
4. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
5. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
6. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
7. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
8. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
9. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
10. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
11. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
12. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
13. a) Allylic transition metal complexes: A. Cutler, D. Ehntholt, W. P. Giering, P. Lennon, S. Raghu, A. Rosan, M. Rosenblum, J. Tancrede, D. Wells, J. Am. Chem. Sac. 1976, 98, 3495; M. Calligaris, G. Carturan, G. Nardin, A. Scrivanti, A. Wojcicki, Organometallics 1983, 2, 865; H. Kurosawa, A. Urabe, K. Miki, N. Kasai, ibid. 1986, 5, 2002; b) allylic silanes: R. L. Danheiser, D. J. Carini, A. Basak, J. Am. Chem. Soc. 1981, 103, 1604; c) trimethylenemethane: B. M. Trost, D. M. T. Chan, ibid. 1979, 101, 6432; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; d) cyclopropenone acetals: D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805; e) nitrones: R. L. Funk, G. L. Bolton, J. U. Daggett, M. M. Hansen, L. H. M. Horcher, Tetrahedron 1985, 41, 3479; W. Oppolzer, S. Siles, R. L. Snowden, B. H. Bakker, M. Petrzilka, ibid. 1985, 41, 3497; A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909; D. P. Curran, C. J. Fenk, Tetrahedron. Lett. 1986, 27, 4865.
14. 2 substrates and 1,3-dianionic building blocks has been reported: G. A. Molander, D. C. Shubert. J. Am. Chem. Soc. 1986, 108, 4683.
15. A. Misumi, K. Iwanaga, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1985, 107, 3343; K. Furuta, A. Misumi, A. Mori, N. Ikeda, H. Yamamoto, Tetrahedron Lett. 1984, 25, 669; A. Misumi, K. Furuta, H. Yamamoto, ibid. 1984, 25, 671.
16. A. Misumi, K. Iwanaga, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1985, 107, 3343; K. Furuta, A. Misumi, A. Mori, N. Ikeda, H. Yamamoto, Tetrahedron Lett. 1984, 25, 669; A. Misumi, K. Furuta, H. Yamamoto, ibid. 1984, 25, 671.
17. A. Misumi, K. Iwanaga, K. Furuta, H. Yamamoto, J. Am. Chem. Soc. 1985, 107, 3343; K. Furuta, A. Misumi, A. Mori, N. Ikeda, H. Yamamoto, Tetrahedron Lett. 1984, 25, 669; A. Misumi, K. Furuta, H. Yamamoto, ibid. 1984, 25, 671.
18. T. Ibuka, T. Aoyagi, F. Yoneda, Y. Yamamoto, J. Organomet. Chem. 1985, 287, C18.
19. -3, 3.13 mL, 5 mmol). After the mixture had been stirred for 30 min at -78°C, trimethylsilyl chloride (0.67 mL, 5.28 mmol) was added dropwise. The solution was stirred for 1 h and then warmed to ambient temperature. The reaction was quenched with water, extracted with diethyl ether, and dried over anhydrous magnesium sulfate. The solvent was evaporated off, and the residue purified by short column chromatography on silica gel with hexane as eluent to give 1 as a white solid in 86% yield (0.93 g, 4.3 mmol). In this case, bis(trimethylsilyl)-substituted carborane was not obtained. The use of a dilute solution of lithium carborane is essential to obtain the monosilylated carborane derivative selectively.
20. In the case of addition of carboranyltributylstannane to cinnamaldehyde catalyzed by palladium, only 1,2-adduct was obtained: H. Nakamura, N. Sadayori, M. Sekido, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1994, 2581.
21. The addition of 1 to aromatic and aliphatic aldehydes promoted by TBAF gave 1,2-adducts in good to high yields: J. Cai, H. Nemoto, H. Nakamura, B. Singaram, Y. Yamamoto, Chem. Lett. 1996, 791.
22. Silyl ether 6 was easily prepared by 1,2-addition of 1-lithio-1,2-dicarba-closo-dodecaborane(12) to crotonaldehyde in THF.
23. The mechanism of this reaction involving a 1,4-addition-proton exchange-addition sequence is quite similar to that of 2,3-bis(phenylsulfonyl)-1,3-butadiene to activated methylenes: A. Padwa, S. S. Murphree, Z. Ni, S. H. Watterson, J. Org. Chem. 1996, 61, 3829.
24. M. F. Hawthorne, Angew. Chem. 1993, 105, 997; Angew. Chem. Int. Ed. Engl. 1993, 32, 950.
25. M. F. Hawthorne, Angew. Chem. 1993, 105, 997; Angew. Chem. Int. Ed. Engl. 1993, 32, 950.