One-pot synthesis of piperidines from imines using 3-stannyl-2-(silylmethyl)propene

Synlett

Volumn , Issue 8, 1998, Pages 921-923

  Kang, Kyung Tae ^a   Kim, Eon Hee ^a   Kim, Won Jeon ^a   Song, Nam Sun ^a   Shin, Jin Kyu ^a   Cho, Bo Young ^a  

^a Pusan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002819588     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1814     Document Type: Article

References (24)

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2. (a) Degl'Innocenti, A.; Dembech, P.; Mordini, A.; Ricci, A.; Seconi, G. Synthesis 1991, 267.
3. (b) Sano, H.; Okawara, M.; Ueno, Y. Synthesis 1984, 933.
4. Keck, G. E.; Palani, A. Tetrahedron Lett. 1993, 34, 3223.
5. Lewis acid or metal catalyst-promoted allylation of aldimines by allylstannanes or allylsilanes leads to homoallylamines regio- and stereoselectively. (a) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883.
6. (b) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289.
7. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
8. (d) Nakamura, H.; Iwama, H.; Yamamoto, Y.; J. Am. Chem. Soc. 1996, 118, 6641 and references therein.
9. (a) Reagent 1b is considerably more reactive than simple allylstannane due to the extra activation provided by the allylic silane substituent. Kang, K. -T.; Sung, T. M.; Kim, J. K.; Kwon, Y. M. Synth. Commun. 1997, 27, 1173.
10. (b) The intermediacy of 3-(trifluorostannyl)-2-(trimethylsilylmethyl)propene and its use in the synthesis of medium sized bicyclic ethers was reported. Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1987, 109, 6877.
11. (c) Clive, D. L. J.; Paul, C. C.; Wang, Z. J. Org. Chem. 1997, 62, 7028.
12. (a) Wang, D. -K.; Dai, L. -X.; Hou, X. -L. Tetrahedron Lett. 1995, 36, 8649.
13. 2 (-78 °C - rt) led to decomposition, while use of boron trifluoride etherate (-78 °C - rt) afforded piperidine 7a in low yield (10 %) only.
14. 23N requires 325.1831], 248 (9), 182 (100), 144 (12), 129 (55), 104 (26), 77 (24).
15. Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954.
16. 3) δ 0.09 (9H, s), 1.58 (2H, s), 2.34 (1H, dd, J = 14.2, 10.2 Hz), 2.52 (1H, dd, J = 14.2, 4.4 Hz), 4.23 (1H, s, br), 4.39 (1H, dd, J = 10.2,4.4 Hz), 4.76 (1H, s), 4.80 (1H, s), 6.47-7.45(10H, m).
17. (a) Grieco, F. A.; Fobare, W. F. Tetrahedron Lett. 1986, 27, 5067
18. (b) Tietze, L. F.; Wunsch, J. R. Angew. Chem. Int. Ed. Engl. 1991, 30, 1697.
19. The reaction of aldimine 3a activated by chlorotrimethylsilane with reagent 1a and benzaldehyde afforded 7a in very low yield (< 5 %).
20. Bell. T. W.; Hu, L. -Y. Tetrahedron Lett. 1988, 29, 4819.
21. 25N requires 339.1987].
22. Murahashi, S. -I.; Naota, T.; Taki, H. J. Chem. Soc. Chem. Commun. 1985, 613.
23. Guiles, J. W.; Meyers, A. I. J. Org. Chem. 1991, 56, 6873.
24. 21N requires 275.1674], 260 (17), 219 (35), 184 (45), 145 (26), 132 (100), 130 (72), 129 (64), 115 (26), 104 (32), 91 (27).