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Systematically Probing the Effect of Catalyst Acidity in a Hydrogen-Bond-Catalyzed Enantioselective Reaction^†

Katrina H. Jensen,
Matthew S. Sigman Prof.

Article first published online: 14 MAY 2007

DOI: 10.1002/anie.200700298

Issue

Angewandte Chemie International Edition

Volume 46, Issue 25, pages 4748–4750, June 18, 2007

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How to Cite

Jensen, Katrina H. and Sigman, Matthew S. (2007), Systematically Probing the Effect of Catalyst Acidity in a Hydrogen-Bond-Catalyzed Enantioselective Reaction. Angew. Chem. Int. Ed., 46: 4748–4750. doi: 10.1002/anie.200700298

Author Information

Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112, USA, Fax: (+1) 801-581-8433

Email: Matthew S. Sigman Prof. (sigman@chem.utah.edu)

^†
This work was supported by the National Science Foundation through a CAREER award to M.S.S. (CHE-132905). M.S.S. thanks the Dreyfus foundation (Teacher-Scholar) and Pfizer for their support.

Publication History

Issue published online: 11 JUN 2007
Article first published online: 14 MAY 2007
Manuscript Revised: 15 MAR 2007
Manuscript Received: 22 JAN 2007

Funded by

National Science Foundation. Grant Number: CHE-132905

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1
M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550–1573;
Direct Link:
Angew. Chem. Int. Ed. 2006, 45, 1520.
Direct Link:
2
P. M. Pihko, Angew. Chem. 2004, 116, 2110–2113;
Direct Link:
Angew. Chem. Int. Ed. 2004, 43, 2062.
Direct Link:
3
P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248–5286;
Direct Link:
Angew. Chem. Int. Ed. 2004, 43, 5138.
Direct Link:
4
W. P. Jencks, Acc. Chem. Res. 1976, 9, 425.
5
W. P. Jencks, Acc. Chem. Res. 1980, 13, 161.
6
P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012.
7
S. Rajaram, M. S. Sigman, Org. Lett. 2005, 7, 5473.
8
A. K. Unni, N. Takenaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336.
9
A. N. Thadani, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. USA 2004, 101, 5846.
10
Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146.
11
Y. Huang, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 9662.
12
J. Hine, S. M. Linden, V. M. Kanagasabapathy, J. Am. Chem. Soc. 1985, 107, 1082.
13
J. Hine, S. M. Linden, V. M. Kanagasabapathy, J. Org. Chem. 1985, 50, 5096.
14
G.-l. Li, G. Zhao, J. Org. Chem. 2005, 70, 4272.
15
F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456.
16
F. G. Bordwell, H. E. Fried, D. L. Hughes, T. Y. Lynch, A. V. Satish, Y. E. Whang, J. Org. Chem. 1990, 55, 3330.
17
See the Supporting Information for details.
18
No appreciable product is observed in the absence of catalyst.
19
R. Gordillo, T. Dudding, C. D. Anderson, K. N. Houk, Org. Lett. 2007, 9, 501.
20
pK_a values were obtained from http://daecr1.harvard.edu/pKa/pka.html
21
E. N. Jacobsen, W. Zhang, M. L. Guler, J. Am. Chem. Soc. 1991, 113, 6703.
22
S.-B. Park, K. Murata, H. Matsumoto, H. Nishiyama, Tetrahedron: Asymmetry 1995, 6, 2487.
23
M. Palucki, N. S. Finney, P. J. Pospisil, M. L. Gueler, T. Ishida, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 948.
24
D. Yang, Y.-C. Yip, J. Chen, K.-K. Cheung, J. Am. Chem. Soc. 1998, 120, 7659.
25
H. Nakagawa, Y. Sei, K. Yamaguchi, T. Nagano, T. Higuchi, Tetrahedron: Asymmetry 2004, 15, 3861.
26
C. L. Perrin, Science 1994, 266, 1665.
27
W. W. Cleland, M. M. Kreevoy, Science 1994, 264, 1887.
28
B. Schwartz, D. G. Drueckhammer, K. C. Usher, S. J. Remington, Biochemistry 1995, 34, 15459.

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Systematically Probing the Effect of Catalyst Acidity in a Hydrogen-Bond-Catalyzed Enantioselective Reaction^†

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Systematically Probing the Effect of Catalyst Acidity in a Hydrogen-Bond-Catalyzed Enantioselective Reaction†

Angewandte Chemie International Edition

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Publication History

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