Selenocyclizations: Control by Coordination and by the Counterion

Angewandte Chemie - International Edition

Volumn 43, Issue 5, 2004, Pages 631-633

  Khokhar, Shaista S ^a   Wirth, Thomas ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Alkenes; Electrophiles; Heterocycles; Selenium; Stereoselective synthesis

Indexed keywords

ADDITIVES; COORDINATION REACTIONS;

ELECTROPHILES; SELECTIVE CYCLIZATIONS;

SELENIUM COMPOUNDS;

ALCOHOL; ALKENE; CARBOXYLIC ACID; HETEROCYCLIC COMPOUND; LACTONE; SELENIUM; TETRAHYDROFURAN;

ARTICLE; CYCLIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 1042274882     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352884     Document Type: Article

References (39)

1. a) Organoselenium Chemistry (Ed.: T. G. Back), Oxford University, Oxford, 1999;
2. b) Topics in Current Chemistry, Vol. 208 (Ed.: T. Wirth), Springer, Berlin, 2000.
3. a) R. Déziel, E. Malenfant, G. Bélanger, J. Org. Chem. 1996, 61, 1875-1876;
4. b) R. Déziel, E. Malenfant, C. Thibault, Tetrahedron Lett. 1998, 39, 5493-5496;
5. c) K.-I. Fujita, K. Murata, M. Iwaoka, S. Tomoda, Tetrahedron 1997, 53, 2029-2048;
6. d) S. Fukuzawa, K. Takahashi, H. Kato, H. Yamazaki, J. Org. Chem. 1997, 62, 7711-7716;
7. e) S. Uemura, Phosphorus Sulfur Relat. Elem. 1998, 136-138, 219-234;
8. f) T. G. Back, S. Nan, J. Chem. Soc. Perkin Trans. 1 1998, 3123-3124;
9. g) T. G. Back, B. P. Dyck, S. Nan, Tetrahedron 1999, 55, 3191-3208;
10. h) T. G. Back, Z. Moussa, Org. Lett. 2000, 2, 3007-3009;
11. i) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L., Bagnoli, A. Temperini, Tetrahedron: Asymmetry 2000, 11, 4645-4650;
12. j) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L. Bagnoli, A. Temperini, Chem. Eur. J. 2002, 8, 1118-1124;
13. k) T. G. Back, Z. Moussa, M. Parvez, J. Org. Chem. 2002, 67, 499-509;
14. l) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L. Bagnoli, A. Temperini, Angew. Chem. 2003, 115, 3239-3241; Angew. Chem. Int. Ed. 2003, 42, 3131-3133.
15. l) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L. Bagnoli, A. Temperini, Angew. Chem. 2003, 115, 3239-3241; Angew. Chem. Int. Ed. 2003, 42, 3131-3133.
16. Reviews: a) M. Tiecco, Top. Curr. Chem. 2000, 208, 7-54;
17. b) T. Wirth, Angew. Chem. 2000, 112, 3890-3900: Angew. Chem. Int. Ed. 2000, 39, 3742-3749.
18. b) T. Wirth, Angew. Chem. 2000, 112, 3890-3900: Angew. Chem. Int. Ed. 2000, 39, 3742-3749.
19. G. Fragale, T. Wirth, Eur J. Org. Chem. 1998, 1361-1369.
20. a) P. L. Beaulieu, R. Déziel in Organoseleninm Chemistry (Ed.: T. G. Back), Oxford University, Oxford, 1999, pp. 35-66;
21. b) N. Petragnani, H. A. Stefani, C. J. Valduga, Tetrahedron 2001, 57, 1411-1448.
22. M. Gruttadauria, C. Aprile, R. Noto, Tetrahedron Lett. 2002, 43, 1669-1672.
23. a) H. Komatsu, M. Iwaoka, S. Tomoda. Chem. Commun. 1999, 205-206;
24. b) M. Spichty, G. Fragale, T. Wirth, J. Am. Chem. Soc. 2000, 122, 10914-10916;
25. c) C. Aprile, M. Gruttadauria, M. E. Amato, F. D'Anna, P. Lo Meo, S. Riela, R. Noto. Tetrahedron 2003, 59, 2241-2251.
26. L. Uehlin, G. Fragale, T. Wirth, Chem. Eur. J. 2002, 8, 1125-1133.
27. Alkene 1 was synthesized by reaction of 3-bromo-2-phenylpropene with the enolate of methyl 3-hydroxypropionate and subsequent hydrolysis of the ester.
28. CCDC-214760 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12. Union Road. Cambridge CB21EZ, UK; fax: (+44) 1223-336-033: or deposit@ ccdc.cam.ac.uk).
29. G. Fragale, T. Wirth. Chem. Eur. J. 1997, 3, 1894-1902.
30. The energies of the tetrahydrofurans 2a and 2b and of the lactones 3a and 3b are almost identical, as shown by ab initio calculations at different levels (6-31G*. 6-311G*).
31. Alkene 4 was synthesized by reduction of 1 with lithium aluminum hydride in 85% yield.
32. a) 2,2′-diselenobisbenzyl alcohol: M. Iwaoka, S. Tomoda, Phosphorus Sulfur Relat. Elem. 1992, 67, 125-130;
33. b) 2.2′-diselenobisbenzoic acid: H. Rosenmund. Ber. Dtsch. Chem. Ges. 1920, 53, 2238;
34. c) methyl 2,2′-diselenobisbenzoate: T. Onami, M. Ikeda, S. S. Woodard, Bull. Chem. Soc. Jpn. 1996, 69, 3601-3605;
35. d) (S,S)-bis[2-(1-hydroxypropyl)-phenyl] diselenides;[11]
36. e) (S,S)-bis-2-(1-methoxymethoxypropyl)phenyl] diselenide;[8]
37. f) (S,S)-bis[2-(1-hydroxyethyl)-6-methoxyphenyl] diselenides.[8]
38. Although not yet determined, we assume, in analogy to earlier experiments, that the structures shown in Scheme 1 represent the absolute configurations of the major diastereomers.
39. Compound 12b was synthesized by addition of carbon dioxide to the enolate of methyl 5-phenyl-4-pentenoate.