New, chiral phase transfer catalysts for effecting asymmetric conjugate additions of α-alkyl-α-cyanoacetates to acetylenic esters

Journal of the American Chemical Society

Volumn 129, Issue 5, 2007, Pages 1038-1039

  Wang, Xisheng ^a   Kitamura, Masanori ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACETYLENE DERIVATIVE; ALKYL GROUP; ESTER DERIVATIVE; NITRILE;

ADDITION REACTION; ALKYLATION; ARTICLE; CATALYST; CHIRALITY; CONJUGATE; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; HYDROLYSIS; PHASE TRANSITION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 33846827094     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068119g     Document Type: Article

References (17)

1. (a) Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999.
2. (b) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
3. (c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 2004; (Suppl. 1).
4. Grossman, R. B.; Comesse, S.; Rasne, R. M.; Hattori, K.; Delong, M. N. J. Org. Chem. 2003, 68, 871.
5. (a) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204.
6. (b) Taylor, M. S.; Zalatan, D. N.; Lerchner, A. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 1313.
7. (c) Li, H.; Song, J.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2005, 127, 8948.
8. (d) Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928.
9. (e) Wu, F.; Hong, R.; Khan, J.; Liu, X.; Deng, L. Angew. Chem., Int. Ed. 2006, 45, 4301. See also related references in ref 3.
10. Successful example of asymmetric conjugate addition of β-diketones to alkynones: Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 5672.
11. (a) Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J., Baro, A., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
12. (b) Douglas, C. J.; Overman. L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363.
13. (c) Denissova. I.; Barriault. L. Tetrahedron 2003, 59, 10105.
14. (a) Kitamura, M.; Shirakawa, S.; Maruoka, K. Angew. Chem. Int. Ed. 2005, 44, 1549.
15. (b) Han, Z.; Yamaguchi, Y.; Kitamura, M.; Maruoka, K. Tetrahedron Lett. 2005, 46, 8555.
16. Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
17. Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439.