Memory of chirality in intramolecular conjugate addition of enolates: A novel access to nitrogen heterocycles with contiguous quaternary and tertiary stereocenters

Organic and Biomolecular Chemistry

Volumn 3, Issue 9, 2005, Pages 1609-1611

  Kawabata, Takeo ^a   Majumdar, Swapan ^a   Tsubaki, Kazunori ^a   Monguchi, Daiki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINO ACIDS; DERIVATIVES; LITHIUM COMPOUNDS; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

CHIRALITY; ETHYL ACETATE; PIPERIDINES; TERTIARY STEREOCENTERS;

STEREOCHEMISTRY;

EID: 18844438937     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b416535g     Document Type: Article

References (23)

1. For recent reviews, see: E. J. Corey and A. Guzman-Perez, Angew Chem., Int. Ed, 1998, 37, 388;
2. J. Christoffers and A. Mann, Angew. Chem., Int. Ed., 2001, 40, 4591.
3. T. Kawabata and K. Fuji, Topics Stereochem., 2003, 23, 175-205.
4. For reactions related to memory of chirality, see: (a) B. Beagley, M. J. Betts, R. G. Pritchard, A. Schofield, R. J. Stoodley and S. Vohra, J. Chem. Soc., Chem. Commun., 1991, 924;
5. (b) M. J. Betts, R. G. Pritchard, A. Schofield, R. J. Stoodley and S. Vohra, J. Chem. Soc., Perkin Trans. 1, 1999, 1067;
6. (c) G. Gerona-Navarro, M. A. Bonache, R. Herranz, M. T. García-López and R. González-Muñiz, J. Org. Chem., 2001, 66, 3538;
7. (d) M. A. Bonache, G. Gerona-Navarro, M. Martín-Martínez, M. T. García-López, P. López, C. Cativiela and R. González-Muñiz, Synlett, 2003, 1007;
8. (e) P. R. Carlier, H. Zhao, J. DeGuzman and P. C.-H. Lam, J. Am. Chem. Soc., 2003, 125, 11482;
9. (f) T. Kawabata, O. Ozturk, H. Suzuki and K. Fuji, Synthesis, 2003, 505;
10. (g) T. Kawabata, S. Kawakami, S. Shimada and K. Fuji, Tetrahedron, 2003, 59, 965.
11. T. Kawabata, H. Suzuki, Y. Nagae and K. Fuji, Angew. Chem., Int. Ed., 2000, 39, 2155-2157.
12. T. Kawabata, S. Kawakami and S. Majumdar, J. Am. Chem. Soc., 2003, 125, 13012-13013.
13. R = 10.9 (2R,3R), 13.4 (2S,3S) min.
14. w = 0.136 (all reflections), GOF = 1.10. CCDC reference number 253569. See http://www.rsc.org/suppdata/ob/b4/b416535g/ for crystallographic data in GIF or other electronic format.
15. K. Shimamoto, M. Ishida, H. Shiozakiand Y. Ohfune, J. Org. Chem., 1991, 56, 4167;
16. A. F. Parsons, Tetrahedron, 1996, 52, 4149.
17. G. T. Wang, Y. Chen, S. Wang, R. Gentles, T. Sowin, W. Kati, S. Muchmore, V. Giranda, K. Stewart, H. Sham, D. Kempf and W. G. Laver, J. Med. Chem., 2001, 44, 1192;
18. D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein and D. J. Kempf, J. Org. Chem., 2002, 67, 5445;
19. C. Chen, X. Li and S. L. Schreiber, J. Am. Chem. Soc., 2003, 125, 10174.
20. S. Hannesian, M. Bayrakdarian and X. Luo, J. Am. Chem. Soc., 2002, 124, 4716;
21. H. He, B. Shen and G. T. Carter, Tetrahedron Lett., 2000, 41, 2067;
22. B. Jiang and M. Xu, Angew. Chem., Int. Ed., 2004, 43, 2543;
23. M. Ori, N. Toda, K. Takami, K. Tago and H. Kogen, Angew. Chem., Int. Ed., 2003, 42, 2540.