Asymmetric synthesis of β-amino cyclic ethers via the intramolecular reaction of γ-alkoxyallylstannane with chiral imine

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1791-1794

  Park, Jung Youl ^a   Park, Choul Hong ^a   Kadota, Isao ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ETHER DERIVATIVE; IMINE; TIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CIS TRANS ISOMERISM; CYCLIZATION; DIASTEREOISOMER; MOLECULAR INTERACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032568220     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10866-8     Document Type: Article

References (19)

1. 1 For recent reviews see: (a) Kleinman, E. F. and Volkmann, R. A. in Comprehensive Organic Synthesis, ed. Trost, B. M. Pergamon Press, New York, 1991, vol. 2, p. 957.
2. (b) Yamamoto, Y. and Asao, N. Chem. Rev. 1993, 93, 2207.
3. (c) Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639.
4. (d) Costa, A. L.; Piazza, A. M.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001.
5. (e) Keck, G. E.; Tabert, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
6. 2 The asymmetric allylation of imines: (a) Yamamoto, Y.; Shinji, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778.
7. (b) Reetz, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
8. The allylation of imines: (c) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289.
9. (d) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641.
10. (e) Kobayashi, S. and Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049.
11. 3 Kadota, I.; Park, J.-Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 841.
12. 4 γ-Alkoxyallylstannane 1 was used for further reaction immediately after the reaction of the aldehyde precursor with (R)-(+)-1-phenylethylamine, since it was decomposed very readily upon treatment with silica-gel column.
13. 3).
14. 6 Nicolaou, K. C.; Hwang, C.-K.; Marron, B. E.; DeFrees, S. A.; Couladouros, E. A.; Abe, Y.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3040.
15. 4, and concentrated. During these processes, the TBS protecting group was removed and 7 was obtained in an almost pure form.
16. 8 (a) Hoffmann, R. W.; Eichler, G.; Endesfelder, A. Liebigs Ann. Chem. 1983, 2000.
17. (b) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Am. Chem. Soc. 1984, 106, 5031.
18. (c) Wuts, P. G. M.; Jung, Y. W. Tetrahedron Lett. 1986, 27, 2079.
19. 4, or TFA was used as an activator, the substrate was decomposed.