No.143
Highly Efficient Asymmetric Organocatalyst
| T2637 | N-(2-Thiophenesulfonyl)-L-prolinamide Trifluoroacetate (1) |
100mg |
In 2000, List et al. reported an intermolecular asymmetric aldol reaction which uses proline as a catalyst.1) List’s report served as a trigger to stimulate research activities in the field of asymmetric organocatalysis.2) The proline derivative 1, which was recently developed by Nakamura et al., shows high TON as an asymmetric catalyst for the asymmetric aldol reaction. Convolutamydine A is an alkaloid that was obtained with high enantioselectivity by using only 0.5 mol% of 1 owing to this high catalytic activity.3) Nakamura shows the reaction mechanism to involve hydrogen bonding between the amide proton of the starting material and the 2-thienyl sulfur atom in 1.
References
1) Proline-catalyzed intermolecular asymmetric aldol reactions
B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395.[DOI]
2) Reviews of asymmetric organocatalyst
a) Special issue on Asymmetric Organocatalysis, Acc. Chem. Res. 2004, 37(8), 487-631. b) H. Pellissier, Tetrahedron 2007, 63, 9267.[DOI]
3) Highly efficient asymmetric organocatalyst, N-(2-thiophenesulfonyl)-L-prolinamide
S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Chem. Eur. J. 2008, 14, 8079.[DOI]
4) First enantioselective synthesis of (R)-convolutamydine B and E
N. Hara, S. Nakamura, N. Shibata, T. Toru, Chem. Eur. J., 2009, 15, 6790.[DOI]
B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395.[DOI]
2) Reviews of asymmetric organocatalyst
a) Special issue on Asymmetric Organocatalysis, Acc. Chem. Res. 2004, 37(8), 487-631. b) H. Pellissier, Tetrahedron 2007, 63, 9267.[DOI]
3) Highly efficient asymmetric organocatalyst, N-(2-thiophenesulfonyl)-L-prolinamide
S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Chem. Eur. J. 2008, 14, 8079.[DOI]
4) First enantioselective synthesis of (R)-convolutamydine B and E
N. Hara, S. Nakamura, N. Shibata, T. Toru, Chem. Eur. J., 2009, 15, 6790.[DOI]
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