Silver-catalyzed enantioselective carbon dioxide incorporation into bispropargylic alcohols

Journal of the American Chemical Society

Volumn 132, Issue 12, 2010, Pages 4072-4073

  Yoshida, Shunsuke ^a   Fukui, Kosuke ^a   Kikuchi, Satoshi ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CARBONS; CATALYST SYSTEM; CHIRAL SCHIFF-BASE; CYCLIC CARBONATES; DESYM-METRIZATION; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; SILVER ACETATE;

CARBON DIOXIDE; FUNCTIONAL GROUPS;

SILVER;

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; CARBON DIOXIDE; CARBONIC ACID DERIVATIVE; SCHIFF BASE; SILVER; SILVER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 77950243421     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1007118     Document Type: Article

References (26)

1. Recent review: Sakakura, T.; Choi, J.-C; Yasuda, H. Chem. Rev. 2007, 107, 2365-2387.
2. (a) Lu, X. B.; Liang, B.; Zhang, Y. J.; Tian, Y. Z.; Wang, Y. M.; Bai, C. X.; Wang, H.; Zhang, R. J. Am. Chem. Soc. 2004, 125, 3732-3733.
3. (b) Paddock, R. L.; Nguyen, S. T. Chem. Commun. 2004, 1622-1623.
4. (c) Barkessel, A.; Brandenburg, M. Org. Lett. 2006, 8, 4401-4404.
5. (d) Chang, T.; Jing, H.; Jin, L.; Ziu, W. J. Mol. Catal. A 2007, 264, 241-247.
6. (e) Chen, S. W.; Kawthekar, R. B.; Kim, G. J. Tetrahedron Lett. 2007, 48, 297-300.
7. (f) Jin, L.; Huang, Y.; Jing, H.; Chang, T.; Yan, P. Tetrahedron: Asymmetry 2008, 19, 1947-1953.
8. (g) Chan, T.; Jing, H. ChemCatChem 2009, 1, 379-383.
9. (h) Yan, P.; Jing, H. Adv. Synth. Catal. 2009, 351, 1325-1332. In polymer synthesis:
10. (i) Lu, X. B.; Wang, Y. Angew. Chem., Int. Ed. 2004, 43, 3574-3577.
11. (j) Paddock, R. L.; Nguyen, S. T. Macromolecules 2005, 38, 6521-16253
12. (k) Shi, L.; Wang, Y. M.; Zhang, R.; Zhang, Y. J.; Peng, X. J.; Zhang, Z. C.; Li, B.; Lu, X. B. J. Am. Chem. Soc. 2006, 128, 1664-1674.
13. (l) Shi, L.; Lu, X. B.; Zhang, R; Peng, X. J.; Zhang, C. Q.; Li, J. F.; Peng, Z. M. Macromolecules 2006, 39, 5679-5685.
14. (m) Li, B.; Wu, G. P.; Ren, W. M.; Wang, Y. M.; Rao, D. Y.; Lu, X. B. J. Polym. Sci, Part A: Polym. Chem. 2008, 45, 6102-6113.
15. (a) Tanaka, H.; Kitaichi, Y.; Sato, M.; Ikeno, T.; Yamada, T. Chem. Lett 2004, 33, 676-677.
16. (b) Yamada, W.; Kitaichi, Y.; Tanaka, H.; Kojima, T.; Sato, M.; Ikeno, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2007, 80, 1391-1401.
17. (a) Nakano, K.; Hiyama, T.; Nozaki, K. J. Am. Chem. Soc. 1999, 121, 11008-11009.
18. (b) Nakano, K.; Hiyama, T.; Nozaki, K. J. Am. Chem. Soc. 2003, 125, 5501-5510.
19. (c) Nakano, K.; Hiyama, T.; Nozaki, K. Chem. Commun.2005, 1871-1873.
20. (d) Cheng, M.; Darling, N. A.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2000, 2007-2008.
21. Takimoto, M.; Nakamura, Y.; Kimura, K; Mori, M. J. Am. Chem. Soc. 2004, 126, 5956-5957.
22. Yamada, W.; Sugawara, Y.; Cheng, H. M.; Ikeno, T.; Yamada, T. Eur. J. Org. Chem. 2007, 2604-2607.
23. Zhang, Y.; Xiang, L.; Wang, Q.; Dua, Q.-F.; Zi, G. Inorg. Chem. Acta 2008, 361, 1246-1254, and references cited therein.
24. See Supporting Information.
25. For the determination of the absolute configuration using VCD spectroscopy: (a) Taniguchi, T.; Monde, K. Trends Glycosci. Glycotechnol. 2007, 19, 147-164.
26. (b) Stephans, P. J.; Devlin, F. J.; Pan, J. J. Chirality 2008, 20, 643-663.