Highly selective thiiranation of 1,2-allenyl sulfones with Br2 and Na2S2O3: Mechanism and asymmetric synthesis of alkylidenethiiranes

Angewandte Chemie - International Edition

Volumn 46, Issue 23, 2007, Pages 4379-4381

  Zhou, Chao ^a   Fu, Chunling ^a   Ma, Shengming ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allenes; Asymmetric synthesis; Electrophilic addition; Regioselectivity; Thiiranes

Indexed keywords

ALLENES; ASYMMETRIC SYNTHESIS; ELECTROPHILIC ADDITION; THIIRANES;

ADDITION REACTIONS; BROMINE COMPOUNDS; CHIRALITY; REGIOSELECTIVITY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

KETONES;

BROMINE; SODIUM THIOSULFATE; SULFONE; THIOL DERIVATIVE; THIOSULFATE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BROMINE; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS; SULFONES; THIOSULFATES;

EID: 34447250129     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700619     Document Type: Article

References (29)

1. For a review on ionic addition to allenes, see: S. Ma in Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, chap. 10, p. 595.
2. a) S. Ma, S. Wu, J. Org. Chem. 1999, 64, 9314;
3. b) S. Ma, S. Wu, Tetrahedron Lett. 2001, 42, 4075;
4. c) C. Fu, S. Ma, Eur. J. Org. Chem. 2005, 3942;
5. d) C. Fu, X. Huang, S. Ma, Tetrahedron Lett. 2004, 45, 6063;
6. e) C. Fu, G. Chen, Y. Deng, X. Huang, S. Ma, Chin. J. Chem. 2004, 22, 990;
7. f) C. Fu, G. Chen, X. Liu, S. Ma, Tetrahedron 2005, 61, 7768.
8. a) S. Ma, X. Hao, X. Huang, Org. Lett. 2003, 5, 1217;
9. b) S. Ma, X. Hao, X. Meng, X. Huang, J. Org. Chem. 2004, 69, 5720.
10. S. Ma, X. Hao, X. Huang, Chem. Commun. 2003, 1082.
11. a) S. Ma, Q. Wei, H. Wang, Org. Lett. 2000, 2, 3893;
12. b) S. Ma, H. Ren, Q. Wei, J. Am. Chem. Soc. 2003, 125, 4817.
13. For a review on the reaction of allenic sulfones, see: T. G. Back, Tetrahedron 2001, 57, 5263.
14. a) A. Padwa, S. S. Murphree, P. E. Yeske, J. Org. Chem. 1990, 55, 4241;
15. b) A. Padwa, M. Ishida, Tetrahedron Lett. 1991, 32, 5673.
16. a) S. Braverman, Y. Duar, J. Am. Chem. Soc. 1983, 105, 1061;
17. b) S. Braverman, D. Reisman, J. Am. Chem. Soc. 1977, 99, 605.
18. For the importance of thiiranes, see: a) M. Lee, M. M. Bernardo, S. O. Meroueh, S. Brown, R. Fridman, S. Mobashery, Org. Lett. 2005, 7, 4463;
19. b) H. Kudo, S. Makino, A. Kameyama, T. Nishikubo, Macromolecules 2005, 38, 5964;
20. c) K. Okuma, T. Shigetomi, Y. Nibu, K. Shioji, M. Yoshida, Y. Yokomori, J. Am. Chem. Soc. 2004, 126, 9508;
21. d) I. T. Lim, S. Brown, S. Mobashery, J. Org. Chem. 2004, 69, 3572;
22. e) W. Adam, R. M. Bargon, Chem. Rev. 2004, 104, 251;
23. f) J. A. Franz, W. J. Shaw, C. N. Lamb, T. Autrey, D. S. Kolwaite, D. M. Camaioni, M. S. Alnajjar, J. Org. Chem. 2004, 69, 1020;
24. g) D.-Q. Yuan, T. Tahara, W.-H. Chen, Y. Okabe, C. Yang, Y. Yagi, Y. Nogami, M. Fukudome, K. Fujita, J. Org. Chem. 2003, 68, 9456;
25. h) W. Adam, R. M. Bargon, W. A. Schenk, J. Am. Chem. Soc. 2003, 125, 3871.
26. int = 0.1155), number of observations: 1764 (I > 2σ(I)), 145 parameters. CCDC-614240 (± -(E)-3m), CCDC-629979 ((S)-(E)-3m), and CCDC-614242 (trans-51) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
27. Optically pure allenyl sulfones were synthesized by the oxidation of chiral allenyl sulfoxides with m-chloroperbenzoic acid in an ice bath. For the synthesis of chiral allenyl sulfoxides, see reference [5b].
28. int = 0.0762), number of observations: 2877 (I > 2σ(I)), 273 parameters; see reference [10].
29. int = 0.1718), number of observations: 1375 (I > 2σ(I)), 184 parameters; see reference [10].