Palladium-catalyzed intramolecular bis-silylation of propargylic alcohols: A new stereospecific access to chiral allenylsilanes

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4884-4885

  Suginome, Michinori ^a   Matsumoto, Akira ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000840216     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960778w     Document Type: Article

References (27)

1. (a) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316.
2. (b) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
3. (c) Fleming, I.; Dunogués, J.; Smithers, R. Org. React. 1989, 37, 57-588.
4. For carbon-carbon double bonds, see: (a) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608-9609. (b) Suginome, M.; Matsumoto, A.; Nagata, K.; Ito, Y. J. Organomet. Chem. 1995, 499, C1-C3. (c) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487-6498. (d) Murakami, M.; Andersson, P. G.; Suginome, M.; Ito, Y. J. Am. Chem. Soc. 1991, 113, 3987-3988.
5. For carbon-carbon double bonds, see: (a) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608-9609. (b) Suginome, M.; Matsumoto, A.; Nagata, K.; Ito, Y. J. Organomet. Chem. 1995, 499, C1-C3. (c) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487-6498. (d) Murakami, M.; Andersson, P. G.; Suginome, M.; Ito, Y. J. Am. Chem. Soc. 1991, 113, 3987-3988.
6. For carbon-carbon double bonds, see: (a) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608-9609. (b) Suginome, M.; Matsumoto, A.; Nagata, K.; Ito, Y. J. Organomet. Chem. 1995, 499, C1-C3. (c) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487-6498. (d) Murakami, M.; Andersson, P. G.; Suginome, M.; Ito, Y. J. Am. Chem. Soc. 1991, 113, 3987-3988.
7. For carbon-carbon double bonds, see: (a) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608-9609. (b) Suginome, M.; Matsumoto, A.; Nagata, K.; Ito, Y. J. Organomet. Chem. 1995, 499, C1-C3. (c) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487-6498. (d) Murakami, M.; Andersson, P. G.; Suginome, M.; Ito, Y. J. Am. Chem. Soc. 1991, 113, 3987-3988.
8. For carbon-carbon triple bonds, see: (a) Murakami, M.; Suginome, M.; Fujimoto, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1473-1475. (b) Murakami, M.; Oike, H.; Sugawara, M.; Suginome, M.; Ito, Y. Tetrahedron 1993, 49, 3933-3946. (c) Ito, Y.; Suginome, M.; Murakami, M. J. Org. Chem. 1991, 56, 1948-1951.
9. For carbon-carbon triple bonds, see: (a) Murakami, M.; Suginome, M.; Fujimoto, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1473-1475. (b) Murakami, M.; Oike, H.; Sugawara, M.; Suginome, M.; Ito, Y. Tetrahedron 1993, 49, 3933-3946. (c) Ito, Y.; Suginome, M.; Murakami, M. J. Org. Chem. 1991, 56, 1948-1951.
10. For carbon-carbon triple bonds, see: (a) Murakami, M.; Suginome, M.; Fujimoto, K.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1473-1475. (b) Murakami, M.; Oike, H.; Sugawara, M.; Suginome, M.; Ito, Y. Tetrahedron 1993, 49, 3933-3946. (c) Ito, Y.; Suginome, M.; Murakami, M. J. Org. Chem. 1991, 56, 1948-1951.
11. Suginome, M.; Matsumoto, A.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3061-3062.
12. (a) Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389-391.
13. (b) Danheiser, R. L.; Kwasigroch, C. A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233-7235.
14. (c) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604-1606.
15. (a) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878.
16. (b) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3927-3929.
17. The MeMgBr reaction did not lead to the formation of an allenylsilane even on warming the reaction mixture at room temperature.
18. The catalytic system was also reported to be effective for bissilylation of carbon-carbon triple bonds. Yamashita, H.; Catellani, M.; Tanaka, M. Chem. Lett. 1991, 241-244.
19. Disubstituted alkynes hardly undergo intermolecular bis-silylation under the conditions; see reif 3.
20. Peterson, D. J. J. Org. Chem. 1968, 33, 780-784.
21. In contrast, similar Peterson elimination of O-lithio-2-(triphenylsilyl)tridecen-3-ol, prepared by the reaction of undecanal with [α-(triphenylsilyl)vinyl]lithium, was reported not to proceed at room temperature in ether. Chan, T. H.; Mychajlowskij, W.; Ong, B. S.; Harpp, D. N. J. Org. Chem. 1978, 43, 1526-1532.
22. For the convenient synthesis of chlorodisilanes via (diethylamino)diphenylsilyllithium, see: (a) Tamao, K.; Kawachi, A.; Nakagawa, Y.; Ito, Y. J. Organomet. Chem. 1994, 473, 29-34. (b) Tamao, K.; Kawachi, A.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 3989-3990.
23. For the convenient synthesis of chlorodisilanes via (diethylamino)diphenylsilyllithium, see: (a) Tamao, K.; Kawachi, A.; Nakagawa, Y.; Ito, Y. J. Organomet. Chem. 1994, 473, 29-34. (b) Tamao, K.; Kawachi, A.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 3989-3990.
24. 2 (2.5 mg, 8.2 μmol) and 1,1,3,3-tetramethylbutyl isocyanide (4.6 mg, 33 μmol) in toluene (1 mL) was added disilanyl ether 1 (0.41 mmol) at room temperature. The mixture was stirred under reflux (bath temperature = 120°C) for 1 h and then cooled to -78°C. A hexane solution of n-BuLi (0.43 mmol) was added at -78°C and then stirred for 20 min. To the mixture was added THF (2 ml) at -78°C, and the mixture was allowed to react at 0°C for 30 min. Extractive workup with ether followed by column chromatography on silica gel (hexane) afforded allenylsilanes 6 in the yields indicated in Table 1.
25. Several attempts at determination of the enantiomeric excess of the optically active allenylsilane by HPLC or GC with chiral stationary phase have failed so far.
26. Enantiomeric excess was determined by HPLC analysis with a chiral stationary phase column, SUMICHIRAL OA-4500.
27. An enantiomerically enriched allenylsilane with an additional stereogenic center o to the allenyl moiety was synthesized by 82′ displacement of a chiral alkynyloxirane with an organocuprate. Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457-1464.