Reaction of Disilylketenes with Organolithiums: New Synthetic Route to Silylacetylene Derivatives

Synlett

Volumn 1996, Issue 7, 1996, Pages 635-636

  Ito, Masato ^a   Shirakawa, Eiji ^a   Takaya, Hidemasa ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009911396     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5579     Document Type: Article

References (18)

1. For a review, Ager, D. J. Org. React. 1990, 38, 1 and references therein. (a) The terms "Peterson olefination" and "Peterson reaction" originally indicate the reaction of an α-silyl organometallic reagent with an aldehyde or ketone to give an olefin. (b) Utimoto, K.; Obayashi, M.; Nozaki, H. J. Org. Chem. 1976, 41, 2940. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Hernandez, D.; Larson, G. L. J. Org. Chem. 1984, 49, 4285. (c) Recently, the first isolation of penta-coordinate 1,2-oxasiletanide, the intermediate of the Peterson reaction, was reported, see; Kawashima, T.; Iwama, N.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 7598.
2. For a review, Ager, D. J. Org. React. 1990, 38, 1 and references therein. (a) The terms "Peterson olefination" and "Peterson reaction" originally indicate the reaction of an α-silyl organometallic reagent with an aldehyde or ketone to give an olefin. (b) Utimoto, K.; Obayashi, M.; Nozaki, H. J. Org. Chem. 1976, 41, 2940. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Hernandez, D.; Larson, G. L. J. Org. Chem. 1984, 49, 4285. (c) Recently, the first isolation of penta-coordinate 1,2-oxasiletanide, the intermediate of the Peterson reaction, was reported, see; Kawashima, T.; Iwama, N.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 7598.
3. For a review, Ager, D. J. Org. React. 1990, 38, 1 and references therein. (a) The terms "Peterson olefination" and "Peterson reaction" originally indicate the reaction of an α-silyl organometallic reagent with an aldehyde or ketone to give an olefin. (b) Utimoto, K.; Obayashi, M.; Nozaki, H. J. Org. Chem. 1976, 41, 2940. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Hernandez, D.; Larson, G. L. J. Org. Chem. 1984, 49, 4285. (c) Recently, the first isolation of penta-coordinate 1,2-oxasiletanide, the intermediate of the Peterson reaction, was reported, see; Kawashima, T.; Iwama, N.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 7598.
4. For a review, Ager, D. J. Org. React. 1990, 38, 1 and references therein. (a) The terms "Peterson olefination" and "Peterson reaction" originally indicate the reaction of an α-silyl organometallic reagent with an aldehyde or ketone to give an olefin. (b) Utimoto, K.; Obayashi, M.; Nozaki, H. J. Org. Chem. 1976, 41, 2940. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Hernandez, D.; Larson, G. L. J. Org. Chem. 1984, 49, 4285. (c) Recently, the first isolation of penta-coordinate 1,2-oxasiletanide, the intermediate of the Peterson reaction, was reported, see; Kawashima, T.; Iwama, N.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 7598.
5. For a review, Ager, D. J. Org. React. 1990, 38, 1 and references therein. (a) The terms "Peterson olefination" and "Peterson reaction" originally indicate the reaction of an α-silyl organometallic reagent with an aldehyde or ketone to give an olefin. (b) Utimoto, K.; Obayashi, M.; Nozaki, H. J. Org. Chem. 1976, 41, 2940. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Hernandez, D.; Larson, G. L. J. Org. Chem. 1984, 49, 4285. (c) Recently, the first isolation of penta-coordinate 1,2-oxasiletanide, the intermediate of the Peterson reaction, was reported, see; Kawashima, T.; Iwama, N.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 7598.
6. For a review, Ager, D. J. Org. React. 1990, 38, 1 and references therein. (a) The terms "Peterson olefination" and "Peterson reaction" originally indicate the reaction of an α-silyl organometallic reagent with an aldehyde or ketone to give an olefin. (b) Utimoto, K.; Obayashi, M.; Nozaki, H. J. Org. Chem. 1976, 41, 2940. Hudrlik, P. F.; Hudrlik, A. M.; Misra, R. N.; Peterson, D.; Withers, G. P.; Kulkarni, A. K. J. Org. Chem. 1980, 45, 4444. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Hernandez, D.; Larson, G. L. J. Org. Chem. 1984, 49, 4285. (c) Recently, the first isolation of penta-coordinate 1,2-oxasiletanide, the intermediate of the Peterson reaction, was reported, see; Kawashima, T.; Iwama, N.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 7598.
7. (a) Woodbury, R. P.; Long, N. R.; Rathke, M. W. J. Org. Chem. 1978, 43, 376.
8. (b) Kita, Y.; Matsuda, S.; Kitagaki, S.; Tsuzuki, Y.; Akai, S. Synlett 1991, 401.
9. Efimova, I. V.; Kazankova, M. A.; Lutsenko, I. F. Zh. Obshch. Khim. 1985, 55, 1647.
10. +).
11. Several attempts to complete the conversion of 2a (R′ = Ph) failed.
12. The products were isolated by preparative HPLC (JAIGel 1H column) using chloroform as an eluent after hydrolytic work-up.
13. Kita, Y.; Tsuzuki, Y.; Kitagaki, S.; Akai, S. Chem. Pharm. Bull. 1994, 42, 233.
14. 2: C, 69.62; H, 7.14. Found: C, 69.72; H, 7.20.
15. Sullivan, D. F.; Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1977, 42, 2038.
16. Sakurai, H.; Shirahata, A.; Sasaki, K.; Hosomi, A. Synthesis, 1979, 740. Also, see ref 3.
17. Wiemer's group reported that halogen-metal exchange of trialkylsiloxyvinyl bromide generated in situ from an α-bromoketone produced acetylenic derivatives as by-products in particular cases, which may arise from β-elimination via 1,3-O to C silyl migration. See; Sampson, P.; Wiemer, D. F. J. Chem. Soc., Chem. Commun. 1985, 1746.
18. Selective nucleophilic attack on silicon was achieved by KOt-Bu-HMPA system. Ito, M.; Shirakawa, E.; Takaya, H. unpublished results.