A new entry to functionalized cycloalkylamines: Diastereoselective intramolecular amidoalkylation of N,O-acetal TMS ether possessing allylsilane

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 573-575

  Jung, Jong Wha ^a   Shin, Dong Yun ^a   Seo, Seung Yong ^a   Kim, Seok Ho ^a   Paek, Seung Mann ^a   Jung, Jae Kyung ^b   Suh, Young Ger ^a  

^a Seoul National University   (South Korea)

^b Chungbuk National University   (South Korea)

Author keywords

Cycloalkylamine; Intramolecular amidoalkylation; N,O Acetal TMS ether

Indexed keywords

ACETAL DERIVATIVE; ALIPHATIC AMINE; SILANE DERIVATIVE;

AMIDOALKYLATION; ARTICLE; CHEMICAL MODIFICATION; MOLECULAR BIOLOGY; STEREOCHEMISTRY;

EID: 11144255716     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.136     Document Type: Article

References (23)

1. For excellent reviews on the chemistry of N-acyliminium ions and the related intermediates, see: W.N. Speckamp, and M.J. Moolenaar Tetrahedron 56 2000 3817 3856
2. H. Hiemstra, and W.N. Speckamp B. Trost I. Fleming Comprehensive Organic Synthesis Vol. 2 1991 Pergamon Oxford 1047 1082
3. For selected recent reports, see: A. Kamatani, and L.E. Overman Org. Lett. 3 2001 129
4. L.E. Overman, and J.P. Wolfe J. Org. Chem. 66 2001 3167
5. M.L. Heredia, E.de la Cuesta, and C. Avendano Tetrahedron: Asymmetry 12 2001 2883
6. W. Chao, J.H. Waldman, and A.M. Weinreb Org. Lett. 5 2003 2915
7. H. Hiemstra, H.P. Fortgens, and W.N. Speckamp Tetrahedron Lett. 26 1985 3155
8. H.F. Mooiweer, H. Hiemstra, H.P. Fortgens, and W.N. Speckamp Tetrahedron Lett. 28 1987 3285
9. Y.-G. Suh, D.-Y. Shin, J.-K. Jung, and S.-H. Kim Chem. Commum. 2002 1064
10. Y.-G. Suh, S.-H. Kim, J.-K. Jung, and D.-Y. Shin Tetrahedron Lett. 43 2002 3165
11. D.-Y. Shin, J.-K. Jung, S.-Y. Seo, Y.-S. Lee, S.-M. Paek, Y.K. Chung, D.M. Shin, and Y.-G. Suh Org. Lett. 5 2003 3635
12. For reviews on cyclic β-amino acids, see: K.-H. Park, and M.J. Kurth Tetrahedron 58 2002 8629
13. M. Liu, and M.P. Sibi Tetrahedron 58 2002 7991
14. W. Tang, S. Wu, and X. Zhang J. Am. Chem. Soc. 125 2003 4976
15. K. Gademann, T. Hintermann, and J.V. Schreiber Curr. Med. Chem. 6 1999 905
16. E.A. Porter, X. Wang, H.-S. Lee, B. Weisblum, and S.H. Gellman Nature 404 2000 565
17. X. Wang, J.F. Espinosa, and S.H. Gellman J. Am. Chem. Soc. 122 2000 4821 and the related references cited therein
18. S.J. Connon, and S. Blechert Angew. Chem., Int. Ed. 42 2003 1900
19. M. Santelli, and J.-M. Pons Lewis Acids and Selectivity in Organic Synthesis 1996 CRC pp 91-177
20. H.H. Wasserman, V.M. Rotello, and G.B. Krause Tetrahedron Lett. 33 1992 5419 The initial introduction of allylic moiety was conducted by reaction of α-bromo-N-p-methoxybenzyl acetamide with allyl mercaptan/NaH, allyl alcohol/NaH and allyl amine, respectively
21. The enamide formation by β-elimination of the acylimium ion rather than allylsilane addition was consistently observed
22. For the trans-ACPC derivative, see: Y. Yokota, G.S. Cortez, and D. Romo Tetrahedron 58 2002 7075 See also Ref. 6
23. The isomer 15 is considered as the major product on the basis of our previous work. Refer to Ref. c