Nitrile anion cyclization with epoxysilanes followed by Brook rearrangement/ring-opening of cyclopropane nitriles/alkylation

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10515-10523

  Okugawa, Seigo ^a   Masu, Hyuma ^b   Yamaguchi, Kentaro ^b   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DERIVATIVES; NEGATIVE IONS; NITROGEN COMPOUNDS;

ANION CYCLIZATION; BROOK REARRANGEMENT; EPOXYSILANES; REACTION PATHWAY;

SILANES;

ACETIC ACID; ALKYLATING AGENT; ANION; BENZYL CYANIDE DERIVATIVE; CYCLOPROPANE DERIVATIVE; DELTA SILYL GAMMA,DELTA EPOXYPENTANITRILE; EPOXIDE; MALONONITRILE; NITRILE; SILANE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ALKYLATION; ALLYLATION; ARTICLE; BROOK REARRANGEMENT; CYCLIZATION; ELIMINATION REACTION; ISOMERIZATION; METHYLATION; REPRODUCIBILITY; RING OPENING; SIMMONS SMITH REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE; X RAY ANALYSIS;

ALKYLATION; CYCLIZATION; CYCLOPROPANES; NITRILES; SILANES;

EID: 28744438005     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0519413     Document Type: Article

References (39)

1. (a) Stork, G.; Cama, L. D.; Coulson, D. R. J. Am. Chem. Soc. 1974, 96, 5268-5270.
2. (b) Stork, G.; Cohen, J. F. J. Am. Chem. Soc. 1974, 96, 5270-5272.
3. (a) Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1-23.
4. (b) Arseniyadis, S.; Kyler, K. S.; Watt, D. S. Org. React. 1984, 31, 1-364.
5. (c) Yamamoto, M.; Yoshitake, M.; Kishikawa, K.; Kohmoto, S. J. Synth. Org. Chem., Jpn. 1992, 50, 638-651.
6. For reviews on Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: New York, 2000.
7. (b) 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.
8. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
9. For the use of Brook rearrangement in tandem bond formation strategies, see: (d) Moser, W. H. Tetrahedron 2001, 57, 2065-2084.
10. Also, see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660.
11. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195.
12. (g) 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, UK, 1995; pp 409-431.
13. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582.
14. (i) Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
15. (a) Takeda, K.; Kawanishi, E.; Sasaki, M.; Takahashi, Y.; Yamaguchi, K. Org. Lett. 2002, 4, 1511-1514.
16. (b) Sasaki, M.; Kawanishi, E.; Nakai, Y.; Matsumoto, T.; Yamaguchi, K.; Takeda, K. J. Org. Chem. 2003, 68, 9330-9339.
17. (c) Matsumoto, M.; Masu, H.; Yamaguchi, K.; Takeda, K. Org. Lett. 2004, 6, 4367-4369.
18. Recently cyclopropane ring opening by a carbanion generated by Brook rearrangement was reported. Clayden, J.; Watson, D. W.; Chambers, M. Tetrahedron 2005, 61, 3195-3203.
19. Corbel, B.; Durst, T. J. Org. Chem. 1976, 41, 3648-3650.
20. (a) Huges, S.; Griffiths, G.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 2 1987, 1253-1264.
21. (b) Stirling, C. J. M. Chem. Rev. 1978, 78, 517-567.
22. For comparison of the α-anion stabilizing ability between phenyl group and trimethylsilyl group, see: Takeda, K.; Ubayama, H.; Sano, A.; Yoshii, E.; Koizumi, T. Tetrahedron Lett. 1998, 39, 5243-5246.
23. Okugawa, S.; Takeda, K. Org. Lett. 2004, 6, 2973-2975.
24. (a) Urabe, H.; Matsuka, T.; Sato, F. Tetrahedron Lett. 1992, 33, 4179-4182.
25. (b) Chen, A. P.-C.; Chen, Y.-H.; Liu, H.-P.; Li, Y.-C.; Chen, C.-T.; Liang, P.-H. J. Am. Chem. Soc. 2002, 124, 15217-15224.
26. This is also supported by the fact that (Z)-13 was formed exclusively irrespective of the countercations. The difference in yield among Li, Na, and K as countercations cannot be explained at present, but possibly it may be due to the difference in the reactivity and stability of the carbanion based on the ionic character of the carbon-metal bond.
27. The relative stereochemistry was not determined.
28. 14 of the structure in the gas phase. Tanaka, K.; Masu, H.; Yamaguchi, K.; Takeda, K. Tetrahedron Lett. 2005, 46, 6429-6432.
29. (a) Antoniotti, P.; Tonachini, G. J. Org. Chem. 1993, 58, 3622-3632.
30. (b) Antoniotti, P.; Canepa, C.; Tonachini, G. J. Org. Chem. 1994, 59, 3952-3959. Also, see:
31. (c) Fleming, I.; Lawrence, A. J.; Richardson, R. D.; Surry, D. S.; West, M. C. Helv. Chim. Acta 2002, 85, 3349-3365.
32. Elimination reactions of α-oxidosilanes with a β-leaving group are known to proceed in an anti manner. Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Soc. 1985, 107, 4260-4264.
33. For discussions on the stereochemistry of Brook rearrangement of α-silyl alkoxides bearing an α,β-leaving group, see: (a) Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609-5617.
34. (b) Also, see ref. 5.
35. Reich, H. J.; Kelly, M. J.; Olson, R. E.; Holtan, R. C. Tetrahedron 1983, 39, 949-960.
36. 25 was obtained as a single isomer and the relative configurations of the nitrile-bearing carbon atom were assigned on the basis of NOESY correlations between the dimethyl group of TBS and the aromatic protons. The relative stereochemistry at C2 and C1′ in 26b was assigned on the basis of literature analogy (ref 20).
37. Takeda, K.; Nakajima, A.; Takeda, M.; Yoshii, E.; Zhang, J.; Boeckman, R. K., Jr. Org. Synth. 1999, 76, 199-213.
38. (a) Sakaguchi, K.; Mano, H.; Ohfune, Y. Tetrahedron Lett. 1998, 39, 4311-4312.
39. (b) Sakaguchi, K.; Higashino, M.; Ohfune, Y. Tetrahedron 2003, 59, 6647-6658.