Building up quarternary stereocenters of chromans by asymmetric redox organocatalysis: A new entry to vitamin e

Angewandte Chemie - International Edition

Volumn 53, Issue 52, 2014, Pages 14313-14315

  Netscher, Thomas ^a  

^a Research and Development   (Switzerland)

Author keywords

Antioxidants; Asymmetric catalysis; Biological activity; Tocopherols; Tocotrienols

Indexed keywords

AMMONIUM IODIDE; CHROMANS; QUATERNARY AMMONIUM COMPOUNDS; TOSYL COMPOUNDS; VITAMIN E;

CATALYSIS; CHEMICAL SYNTHESIS; CHEMISTRY; OXIDATION-REDUCTION; STEREOISOMERISM;

CATALYSIS; CHROMANS; OXIDATION-REDUCTION; QUATERNARY AMMONIUM COMPOUNDS; STEREOISOMERISM; TOSYL COMPOUNDS; VITAMIN E;

EID: 84919683867     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409826     Document Type: Article

References (39)

1. a) H. C. Shen, Tetrahedron 2009, 65, 3931-3952;
2. b) M. G. Núñez, P. García, R. F. Moro, D. Díez, Tetrahedron 2010, 66, 2089-2109;
3. c) M. L. Colombo, Molecules 2010, 15, 2103-2113;
4. d) T. Netscher, Vitam. Horm. 2007, 76, 155-202 and references therein.
5. a) G. W. Burton, K. U. Ingold, Acc. Chem. Res. 1986, 19, 194-201;
6. b) J. Weimann, H. Weiser, Am. J. Clin. Nutr. 1991, 53,1056S-1060S;
7. c) H. Weiser, M. Vecchi, Int. J. Vit. Nutr. Res. 1982, 52, 351-370.
8. a) R. Noyori, Angew. Chem. Int. Ed. 2002, 41, 2008-2022;
9. Angew. Chem. 2002, 114, 2108-2123;
10. b) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345-350;
11. c) T. Netscher, M. Scalone, R. Schmid in Asymmetric Catalysis on Industrial Scale (Eds.: H.- U. Blaser, E. Schmidt),Wiley-VCH,Weinheim, 2004, pp. 71-89;
12. d) D. H. Woodmansee, A. Pfaltz, Chem. Commun. 2011, 47, 7912-7916;
13. e) D. H. Woodmansee, A. Pfaltz, Top. Organomet. Chem. 2011, 34, 31-76.
14. a) B. M. Trost, J. Org. Chem. 2004, 69, 5813-5837;
15. b) B. M. Trost, H. C. Shen, L. Dong, J.-P. Surivet, C. Sylvain, J. Am. Chem. Soc. 2004, 126, 11966-11983;
16. c) B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1998, 120, 9074-9075.
17. a) L. F. Tietze, F. Strecker, J. Zinngrebe, K. M. Sommer, Chem. Eur. J. 2006, 12, 8770-8776;
18. b) L. F. Tietze, K. M. Sommer, J. Zinngrebe, F. Strecker, Angew. Chem. Int. Ed. 2005, 44, 257-259;
19. Angew. Chem. 2005, 117, 262-264;
20. for the catalytic asymmetric Wacker-type cyclization to chromans see: Y. Uozumi, K. Kato, T. Hayashi, J. Am. Chem. Soc. 1997, 119, 5063-5064.
21. a) Science of Synthesis: Asymmetric Organocatalysis (Eds.: B. List, K. Maruoka), Georg Thieme, Stuttgart, 2012;
22. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis (Eds.: A. Berkessel, H. Grçger), Wiley-VCH, Weinheim, 2007;
23. c) A. Dondoni, A. Massi, Angew. Chem. Int. Ed. 2008, 47, 4638-4660;
24. Angew. Chem. 2008, 120, 4716-4739;
25. d) A. Moyano, R. Rios, Chem. Rev. 2011, 111, 4703-4832.
26. a) A. Chougnet, K. Liu, W.-D. Woggon, Chimia 2010, 64, 303-308;
27. b) K. Liu, A. Chougnet, W.-D. Woggon, Angew. Chem. Int. Ed. 2008, 47, 5827-5829;
28. Angew. Chem. 2008, 120, 5911-5913.
29. a)W.-D. Woggon, Angew. Chem. 1999, 111, 2881-2883;
30. Angew. Chem. Int. Ed. 1999, 38, 2715-2716;
31. b) D. Shintani, D. DellaPenna, Science 1998, 282, 2098-2100.
32. a) M. Uyanik, H. Hayashi, K. Ishihara, Science 2014, 345, 291-294;
33. b) B. J. Nachtsheim, Science 2014, 345, 270-271;
34. c) S. Borman, Chem. Eng. News 2014, 92(29), 8; for earlier work on this topic see:
35. d) M. Uyanik, H. Okamoto, T. Yasui, K. Ishihara, Science 2010, 328, 1376-1379;
36. e) A. N. French, Science 2010, 328, 1365-1366;
37. f) S. Everts, Chem. Eng. News 2010, 88(24), 11.
38. T. Ooi, K. Maruoka, Angew. Chem. Int. Ed. 2007, 46, 4222-4266;
39. Angew. Chem. 2007, 119, 4300-4345.