An aza-brook rearrangement of (α-silylallyl)amine

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1196-

  Honda, Takahiro ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001324975     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952116x     Document Type: Article

References (10)

1. Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
2. Yamamoto, Y. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 1, p 55.
3. For the synthesis of (α-silylalkyl)amine: (a) Okazaki, S.; Sato, Y. Synthesis 1990, 36. (b) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem, Soc. 1994, 116, 3231. (c) Sakuragi, A.; Shirai, N.; Sato, Y.; Kurono, Y.; Hatano, K. J. Org. Chem. 1994, 59, 148. (d) Labrecque, D.; Nwe, K T.; Chan, T. H. Organometallics 1994, 13, 332. (e) Katritzky, A. R.; Hong, Q.; Yang, Z. Organometallics 1995, 14, 734. (f) Murai, T.; Oda, T.; Kimura, F.; Onishi, H.; Kanda, T.; Kato, S. J. Chem. Soc., Chem. Commun. 1994, 2143.
4. For the synthesis of (α-silylalkyl)amine: (a) Okazaki, S.; Sato, Y. Synthesis 1990, 36. (b) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem, Soc. 1994, 116, 3231. (c) Sakuragi, A.; Shirai, N.; Sato, Y.; Kurono, Y.; Hatano, K. J. Org. Chem. 1994, 59, 148. (d) Labrecque, D.; Nwe, K T.; Chan, T. H. Organometallics 1994, 13, 332. (e) Katritzky, A. R.; Hong, Q.; Yang, Z. Organometallics 1995, 14, 734. (f) Murai, T.; Oda, T.; Kimura, F.; Onishi, H.; Kanda, T.; Kato, S. J. Chem. Soc., Chem. Commun. 1994, 2143.
5. For the synthesis of (α-silylalkyl)amine: (a) Okazaki, S.; Sato, Y. Synthesis 1990, 36. (b) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem, Soc. 1994, 116, 3231. (c) Sakuragi, A.; Shirai, N.; Sato, Y.; Kurono, Y.; Hatano, K. J. Org. Chem. 1994, 59, 148. (d) Labrecque, D.; Nwe, K T.; Chan, T. H. Organometallics 1994, 13, 332. (e) Katritzky, A. R.; Hong, Q.; Yang, Z. Organometallics 1995, 14, 734. (f) Murai, T.; Oda, T.; Kimura, F.; Onishi, H.; Kanda, T.; Kato, S. J. Chem. Soc., Chem. Commun. 1994, 2143.
6. For the synthesis of (α-silylalkyl)amine: (a) Okazaki, S.; Sato, Y. Synthesis 1990, 36. (b) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem, Soc. 1994, 116, 3231. (c) Sakuragi, A.; Shirai, N.; Sato, Y.; Kurono, Y.; Hatano, K. J. Org. Chem. 1994, 59, 148. (d) Labrecque, D.; Nwe, K T.; Chan, T. H. Organometallics 1994, 13, 332. (e) Katritzky, A. R.; Hong, Q.; Yang, Z. Organometallics 1995, 14, 734. (f) Murai, T.; Oda, T.; Kimura, F.; Onishi, H.; Kanda, T.; Kato, S. J. Chem. Soc., Chem. Commun. 1994, 2143.
7. For the synthesis of (α-silylalkyl)amine: (a) Okazaki, S.; Sato, Y. Synthesis 1990, 36. (b) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem, Soc. 1994, 116, 3231. (c) Sakuragi, A.; Shirai, N.; Sato, Y.; Kurono, Y.; Hatano, K. J. Org. Chem. 1994, 59, 148. (d) Labrecque, D.; Nwe, K T.; Chan, T. H. Organometallics 1994, 13, 332. (e) Katritzky, A. R.; Hong, Q.; Yang, Z. Organometallics 1995, 14, 734. (f) Murai, T.; Oda, T.; Kimura, F.; Onishi, H.; Kanda, T.; Kato, S. J. Chem. Soc., Chem. Commun. 1994, 2143.
8. For the synthesis of (α-silylalkyl)amine: (a) Okazaki, S.; Sato, Y. Synthesis 1990, 36. (b) Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem, Soc. 1994, 116, 3231. (c) Sakuragi, A.; Shirai, N.; Sato, Y.; Kurono, Y.; Hatano, K. J. Org. Chem. 1994, 59, 148. (d) Labrecque, D.; Nwe, K T.; Chan, T. H. Organometallics 1994, 13, 332. (e) Katritzky, A. R.; Hong, Q.; Yang, Z. Organometallics 1995, 14, 734. (f) Murai, T.; Oda, T.; Kimura, F.; Onishi, H.; Kanda, T.; Kato, S. J. Chem. Soc., Chem. Commun. 1994, 2143.
9. Honda, T.; Satoh, S.; Mori, M. Organometallics 1995, 14, 1548.
10. Compound 9 was formed by migration of the silyl group from the nitrogen to the γ carbon of N-(silylallyl)anion 10 and subsequent N-methylation.