Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols

Journal of the American Chemical Society

Volumn 134, Issue 9, 2012, Pages 4096-4099

  Wang, Yan ^a   Zheng, Kuan ^a   Hong, Ran ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOISOMERIZATIONS; KINETIC RESOLUTION; MECHANISTIC MODELS;

CATALYSIS; FUNCTIONAL GROUPS; STEREOSELECTIVITY;

PHOSPHATES;

ALCOHOL; CHIRAL SILVER PHOSPHATE; FUNCTIONAL GROUP; PHOSPHATE; PROPADIENOL; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOISOMERIZATION; ISOMERIZATION; KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALCOHOLS; ALKADIENES; CATALYSIS; CYCLIZATION; KINETICS; MOLECULAR STRUCTURE; PHOSPHATES; SILVER COMPOUNDS; STEREOISOMERISM;

EID: 84863230403     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300453u     Document Type: Article

References (38)

1. (a) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
2. (b) Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657.
3. (c) Krause, N.; Winter, N. Chem. Rev. 2011, 111, 1994.
4. (d) Pradal, A.; Toullec, P. Y.; Michelet, V. Synthesis 2011, 1501.
5. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496.
6. Silver in Organic Chemistry; Harmata, M., Ed.; Wiley: Hoboken, NJ, 2010.
7. Leandri, G.; Monti, H.; Bertrand, M. Tetrahedron 1974, 30, 289.
8. (a) Modern Allene Chemistry; Krause, N., Hashimi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
9. (b) Deng, Y.-Q.; Gu, Z.-H.; Ma, S.-M. Chin. J. Org. Chem. 2006, 26, 1468.
10. (c) Yu, S.; Ma, S. Chem. Commun. 2011, 47, 5384.
11. (a) Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447.
12. (b) Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878.
13. (c) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130.
14. (a) Iseki, K.; Kuroki, Y.; Kobayashi, Y. Tetrahedron: Asymmetry 1998, 9, 2889.
15. (b) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449.
16. (a) Yu, C.-M.; Yoon, S.-K.; Baek, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392.
17. (b) Inoue, M.; Nakada, M. Angew. Chem., Int. Ed. 2006, 45, 252.
18. (c) Xia, G.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 496.
19. (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1990, 112, 6129.
20. (b) Xu, D.; Li, Z.; Ma, S. Chem.-Eur. J. 2002, 8, 5012.
21. Yu, C.-M.; Kim, C.; Kweon, J. H. Chem. Commun. 2004, 2494.
22. N2′-type reaction to prepare chiral α-allenic alcohols was reported with two examples. See: Kang, S.-K.; Kim, D.- Y.; Rho, H.-S.; Yoon, S.-H.; Ho, P.-S. Synth. Commun. 1996, 26, 1485.
23. Wang, Y.; Zhu, L.; Zhang, Y.; Hong, R. Angew. Chem., Int. Ed. 2011, 50, 2787.
24. For leading references, see: (a) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417.
25. (b) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200.
26. (a) Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. J. Am. Chem. Soc. 2010, 132, 4072.
27. (b) Rauniyar, V.; Wang, Z. J.; Burks, H. E.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 8486.
28. (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
29. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
30. (c) Terada, M. Synthesis 2010, 1929.
31. (a) Hatano, M.; Moriyama, K.; Maki, T.; Ishihara, K. Angew. Chem., Int. Ed. 2010, 49, 3823.
32. (b) Klussmann, M.; Ratjen, L.; Hoffmann, S.; Wakchaure, V.; Goddard, R.; List, B. Synlett 2010, 2189.
33. (c) Terada, M.; Kanomata, K. Synlett 2011, 1255.
34. (a) Nagendrappa, G.; Joshi, G. C.; Devaprabhakara, D. J. Organomet. Chem. 1971, 27, 421.
35. (b) Chenier, J. H. B.; Howard, J. A.; Mile, B. J. Am. Chem. Soc. 1985, 107, 4190.
36. (a) Brown, T. J.; Sugie, A.; Dickens, M. G.; Widenhoefer, R. A. Organometallics 2010, 29, 4207.
37. (b) Gandon, V.; Lemière, G.; Hours, A.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2008, 47, 7534.
38. The gram-scale syntheses of 1a and 1s and their synthetic applications are exemplified in the SI.