Reaction of acylsilanes with potassium cyanide: Brook rearrangement under phase-transfer catalytic conditions

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4169-4172

  Takeda, Kei ^a   Ohnishi, Yuji ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Cyanides; Cyanohydrins; Cyclization; Rearrangements; Silicon and compounds

Indexed keywords

CYANOHYDRIN; CYCLOPROPANE DERIVATIVE; POTASSIUM CYANIDE; SILANE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CYCLIZATION; LIQUID LIQUID EXTRACTION; PHASE TRANSITION;

EID: 0034729469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00560-8     Document Type: Article

References (25)

1. For reviews on acylsilanes, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000.
2. (b) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W.; Moody, C. J., Eds.; Pergamon: Oxford, 1995, pp. 409-431.
3. (c) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582.
4. (d) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195.
5. (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660.
6. For reviews on the Brook rearrangement, see: (a) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp. 149-221.
7. (b) Brook, A. G. Acc. Chem. Res., 1974, 7, 77-84. Also see: Ref. 1a.
8. (a) Takeda, K.; Nakajima, A.; Takeda, M.; Yoshii, E.; Zhang, J.; Boeckman Jr., R. K. Org. Synth. 1999, 76, 199-213.
9. (b) Takeda, K.; Ohtani, Y. Org. Lett. 1999, 1, 677-679.
10. (c) Takeda, K.; Tanaka, T. Synlett 1999, 705-708.
11. (d) Takeda, K.; Nakajima, A.; Takeda, M.; Okamoto, Y.; Sato, T.; Yoshii, E.; Koizumi, T.; Shiro, M. J. Am. Chem. Soc. 1998, 120, 4947-4959.
12. (e) Takeda, K.; Ohtani, Y.; Ando, E.; Fujimoto, K.; Yoshii, E.; Koizumi, T. Chem. Lett. 1998, 1157-1158.
13. (f) Takeda, K.; Nakajima, A.; Yoshii, E. Synlett 1996, 753-754.
14. (g) Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401.
15. (h) Takeda, K.; Nakatani, J.; Nakamura, H.; Sako, K.; Yoshii, E.; Yamaguchi, K. Synlett 1993, 841-843.
16. (i) Takeda, K.; Fujisawa, M.; Makino, T.; Yoshii, E.; Yamaguchi, K. J. Am. Chem. Soc. 1993, 115, 9351-9352.
17. Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609-5617.
18. Pietropaolo, D.; Fiorenza, M.; Ricci, A.; Taddei, M. J. Organomet. Chem. 1980, 197, 7-11.
19. Nowick, J. S.; Danheiser, R. L. J. Org. Chem. 1989, 54, 2798-2802. Also see: Ref. 3d.
20. 3, and concentrated. The residual oil was subjected to column chromatography (silica gel, 15 g; elution with hexane-AcOEt=30:1) to give 4.
21. 2 resulted in lower yields of 4 and/or in the recovery of starting material. This may be partly attributed to the lower stability of the generated carbanion in the solvents. Under the PTC conditions, the carbanion can be immediately protonated.
22. 10 with MeOH in the presence of p-TsOH.
23. Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949-960.
24. For the formation of cyclopropane derivatives by the reaction of β-chloroacylsilane and phenyllithium followed by the Brook rearrangement, see: Ref. 4.
25. Stork, G.; Depezay, J. C.; d'Angelo, J. Tetrahedron Lett. 1975, 389-392.