Diversity-generation from an allenoate-enone coupling: Syntheses of azepines and pyrimidones from common precursors

Tetrahedron

Volumn 61, Issue 26, 2005, Pages 6309-6314

  Evans, Catherine A ^a   Cowen, Bryan J ^a   Miller, Scott J ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

Azacycle; Heterocycle; Quinuclidine

Indexed keywords

AZEPINE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 20444449320     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.106     Document Type: Article

References (27)

1. For an excellent review on 7, 8, and 9-membered azacycle synthesis and natural products, see (a) P.A. Evans, and A.B. Holmes Tetrahedron 47 1991 9131 9166
2. D. O'Hagan Nat. Prod. Rep. 1997 637 652
3. For a discussion on the novel biological activity of glucose-derived 7-membered azasugars, see: D.D. Dhavale, S.D. Markad, N.S. Karanjule, and J. PrakashaReddy J. Org. Chem. 69 2004 4760 4766
4. C.A. Evans, and Miller J. Am. Chem. Soc. 125 2003 12394 12395
5. The quinuclidine-catalyzed reaction initiates through conjugate addition, in analogy to the amine-catalyzed Baylis-Hilman reaction. For a review, see: D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
6. For several key references to nucleophilic catalysis via conjugate addition of P-nucleophiles, see (a) B.M. Trost, and U. Kazmaier J. Am. Chem. Soc. 114 1992 7933 7935
7. C. Guo, and X. Lu J. Chem. Soc., Perkin Trans. 1 1993 1921 1923
8. B.M. Trost, and G.R. Dake J. Am. Chem. Soc. 119 1997 7595 7596
9. B.M. Trost, and G.R. Dake J. Org. Chem. 62 1997 5670 5671
10. L.-C. Wang, A.-L. Luis, K. Agapiou, H.-Y. Jang, and M.J. Krische J. Am. Chem. Soc. 124 2002 2402 2403
11. S.A. Frank, D.J. Mergott, and W.R. Roush J. Am. Chem. Soc. 124 2002 2404 2405
12. J.-C. Wang, S.-S. Ng, and M.J. Krische J. Am. Chem. Soc. 125 2003 3682 3683
13. Vinyl ketone derivatives of α-amino acids are readily obtained in analogy to the following precedents: (a) A. Spaltenstein, J.J. Leban, J.J. Huang, K.R. Reinhardt, O.H. Viveros, J. Sigafoos, and R. Crouch Tetrahedron Lett. 37 1996 1343 1346
14. S. Nahm, and S.M. Weinreb Tetrahedron Lett. 22 1981 3815 3818 (c) At this stage, we have not evaluated the extent to which racemization may have occurred at any step in the sequences
15. For recent reviews concerning syntheses of 7- and 8-membered azacycles, see: (a) A. Deiters, and S.F. Martin Chem. Rev. 104 2004 2199 2238
16. I. Nakamura, and Y. Yamamoto Chem. Rev. 104 2004 2127 2198
17. C. Mukai, H. Yamashita, and M. Hanaoka Org. Lett. 3 2001 3385 3387
18. C. Mukai, R. Ukon, and N. Kuroda Tetrahedron Lett. 44 2003 1583 1586
19. C. Mukai, M. Kobayashi, S. Kubota, Y. Takahashi, and S. Kitagaki J. Org. Chem. 69 2004 2128 2136
20. As noted in Ref. 6, product racemization has not yet been evaluated in these sequences. Circumstantially, we note that product 19 was isolated without erosion of diastereomeric purity.
21. R.M. Acheson, M.G. Bite, and M.W. Cooper J. Chem. Soc., Perkin Trans. 1 1976 1908 1911
22. G.J.S. Doad, D.I. Okor, F. Scheinmann, P.A. Bates, and M.B. Hursthouse J. Chem. Soc., Perkin Trans. 1 1988 2993 3003
23. Compound 24 is isolated as a mixture of diastereomers (∼1:1 cis/trans) after pyrimidone formation.
24. X. Lu, C. Zhang, and Z. Xu Acc. Chem. Res. 34 2001 535 544 and references therein
25. Y. Du, X. Lu, and Y. Yu J. Org. Chem. 67 2002 8901 8905
26. X.-F. Zhu, J. Lan, and O. Kwon J. Am. Chem. Soc. 125 2003 4716 4717
27. X.-F. Zhu, C.E. Henry, J. Wang, T. Dudding, and O. Kwon Org. Lett. 7 2005 1387 1390