An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from β-heteroatom amino compounds and vinyl sulfonium salts

Angewandte Chemie - International Edition

Volumn 47, Issue 20, 2008, Pages 3784-3786

  Yar, Muhammad ^a   McGarrigle, Eoghan M ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Annulation; Heterocycles; Morpholines; Vinyl sulfonium salts; Ylides

Indexed keywords

AMINES; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS; ETHANE; SYNTHESIS (CHEMICAL);

ANNULATION; HETEROCYCLES; MORPHOLINES; VINYL SULFONIUM SALTS; YLIDES;

COMPLEXATION;

AMINE; INORGANIC SALT; MORPHOLINE DERIVATIVE; PIPERAZINE DERIVATIVE; SULFONIUM DERIVATIVE; THIOMORPHOLINE;

ARTICLE; CHEMISTRY; SYNTHESIS;

AMINES; MORPHOLINES; PIPERAZINES; SALTS; SULFONIUM COMPOUNDS;

EID: 45549086270     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800373     Document Type: Article

References (44)

1. For a review see: a) R. Wijtmans, M. K. S. Vink, H. E. Schoemaker, F. L. van Delft, R. H. Blaauw, F. P. J. T. Rutjes, Synthesis 2004, 641-662;
2. for recent examples see: b) M. Breuning, M. Winnacker, M. Steiner, Eur. J. Org. Chem. 2007, 2100-2106;
3. c) M. D'hooghe, T. Vanlangendonck, K. W. Törnroos, N. De Kimpe, J. Org. Chem. 2006, 71, 4678-4681;
4. d) R. Pedrosa, C. Andrés, P. Mendiguchía, J. Nieto, J. Org. Chem. 2006, 71, 8854-8863;
5. e) M. C. Wilkinson, Tetrahedron Lett. 2005, 46, 4773-4775;
6. f) B. A. Lanman, A. G. Myers, Org. Lett. 2004, 6, 1045-1047.
7. a) H. Chiu, Y. C. Lin, C. Y. Cheng, M. C. Tsai, H. C. Yu, Bioorg. Med. Chem. Lett. 2001, 9, 383-393;
8. b) C. Kashima, K. Harada, J. Chem. Soc. Perkin Trans. 1 1988, 1521-1526;
9. c) P. H. Liang, L. W. Hsin, C. Y. Cheng, Bioorg. Med. Chem. 2002, 10, 3267-3276;
10. d) K. Sakai, N. Yoneda, Chem. Pharm. Bull. 1981, 29, 1554-1560;
11. e) U. Bhatt, G. Just, Helv. Chim. Acta 2000, 83, 722-727.
12. a) K. E. Henegar, M. Cebula, Org. Process Res. Dev. 2007, 11, 354-358;
13. b) E. Brenner, R. M. Baldwin, G. Tamagnan, Org. Lett. 2005, 7, 937-939;
14. c) A. Meinzer, A. Breckel, B. A. Thaher, N. Manicone, H.-H. Otto, Helv. Chim. Acta 2004, 87, 90-105;
15. d) J. Prabhakaran, V. J. Majo, J. J. Mann, J. S. Dileep Kumar, Chirality 2004, 16, 168-173;
16. e) naphthol derivatives: Jpn. Kokai Tokkyo Koho, Patent JP 57163356, 1982;
17. f) A. Viso, R. F. de La Pradilla, A. Flores, A. García, M. Tortosa, M. L. López-Rodríguez, J. Org. Chem. 2006, 71, 1442-1448.
18. For vinyl sulfonium salts see: a) M. G. Unthank, N. Hussain, V. K. Aggarwal, Angew. Chem. 2006, 118, 7224-7227;
19. Angew. Chem. Int. Ed. 2006, 45, 7066-7069;
20. b) K. Kim, L. S. Jimenez, Tetrahedron: Asymmetry 2001, 12, 999-1005, and references therein;
21. c) Y. Wang, W. Zhang, V. J. Colandrea, L. S. Jimenez, Tetrahedron 1999, 55, 10659-10672;
22. for epoxidation reactions of butadienylsulfonium salts see: d) M. W. Rowbottom, N. Mathews, T. Gallagher, J. Chem. Soc. Perkin Trans. 1 1998, 3927-3929;
23. for recent examples of the application of vinyl phosphonium salts see: e) S. Kumarn, D. M. Shaw, S. V. Ley, Chem. Commun. 2006, 3211-3213.
24. Nucleophiles with two acidic protons on the same atom have been shown to react with vinyl sulfonium salts to give 3-membered rings: a) J. Gosselck, L. Béress, H. Schenk, Angew. Chem. 1966, 78, 606;
25. Angew. Chem. Int. Ed. Engl. 1966, 5, 596-597;
26. b) C. R. Johnson, J. P. Lockard, Tetrahedron Lett. 1971, 12, 4589-4592;
27. c) K. Takaki, T. Agawa, J. Org. Chem. 1977, 42, 3303-3304;
28. d) J. Matsuo, H. Yamanaka, A. Kawana, T. Mukaiyama, Chem. Lett. 2003, 32, 392-393;
29. where the nucleophile can be resonance-stabilized forming an enolate, five-membered rings have also been obtained: e) H. Braun, G. Huber, Tetrahedron Lett. 1976, 17, 2121-2124;
30. f) J. W. Batty, P. D. Howes, C. J. M. Stirling, J. Chem. Soc. Perkin Trans. 1 1973, 65-68; ref. [5b].
31. 3 (30.8). See J.-P. Cheng, B. Liu, Y. Zhao, Y. Sun, X.-M. Zhang, Y. Lu, J. Org. Chem. 1999, 64, 604-610.
32. V. K. Aggarwal, J. N. Harvey, R. Robiette, Angew. Chem. 2005, 117, 5604-5607;
33. Angew. Chem. Int. Ed. 2005, 44, 5468-5471.
34. This was found to be generally superior to dialkylvinyl sulfonium salts. See Supporting Information for further details.
35. This salt, and its precursor, will soon be commercially available from Aldrich.
36. 2O, have been reported to add to the vinyl sulfonium salt in the presence of base. W. von E. Doering, K. C. Schreiber, J. Am. Chem. Soc. 1955, 77, 514-520.
37. These were more successful than primary amine (unprotected), amide, or carbamate groups. See Supporting Information for further details.
38. See ref. [5d] and Supporting Information for further details of aziridine formation from unprotected β-amino alcohols.
39. F. Sladojevich, A. Trabocchi, A. Guarna, J. Org. Chem. 2007, 72, 4254-4257.
40. a) J. I. Levin, J. M. Chen, L. M. Laakso, M. Du, X. Du, A. M. Venkatesan, V. Sandanayaka, A. Zask, J. Xu, W. Xu, Y. Zhang, J. S. Skotnicki, Bioorg. Med. Chem. Lett. 2005, 15, 4345-4349;
41. b) N. G. Almstead, R. S. Bradley, S. Pikul, B. De, M. G. Natchus, Y. O. Taiwo, F. Gu, L. E. Williams, B. A. Hynd, M. J. Janusz, C. M. Dunaway, G. E. Mieling, J. Med. Chem. 1999, 42, 4547-4562;
42. c) J. Chiba, N. Machinaga, T. Takashi, A. Ejima, G. Takayama, M. Yokoyama, A. Nakayama, J. J. Baldwin, E. McDonald, K. W. Saionz, R. Swanson, Z. Hussain, A. Wong, Bioorg. Med. Chem. Lett. 2005, 15, 41-45.
43. J. E. Baldwin, A. C. Spivey, C. J. Schofield, J. B. Sweeney, Tetrahedron 1993, 49, 6309-6330.
44. L. Sannamu, N. Kosaku, A. Haruhiko, K. Tetsuo, N. Izumiya, Int. J. Pept. Protein Res. 1986, 27, 44-50.