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Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid
Open accessAbstract
The development of catalysts for Mannich-type reactions that afford anti-products with excellent diastereo- and enantioselectivities under mild conditions and low catalyst loadings (1-5 mol %) is reported. Based on principles gained from the study of (S)-proline-catalyzed Mannich-type reactions that afford enantiomerically enriched syn-products, (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid (RR35) has been designed to catalyze the direct enantioselective anti-selective Mannich-type reactions. Computational studies of the above reaction using HF/6-31G* level of theory suggested that this design would be highly effective. The catalyst was subsequently synthesized and studied in organocatalytic Mannich-type reactions between unmodified aldehydes and N-PMP-protected alpha-imino esters. In accord with the design principles and in quantitative agreement with the theoretical predictions, reactions catalyzed by this catalyst afforded anti-products in good yields with excellent diastereo- and enantioselectivities (anti:syn 94:6 to 98:2, >97 to >99% ee).
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Cited by
Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Asymmetrische Organokatalyse: Eintritt in die Reifezeit
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie · doi:10.1002/ange.200704684 · Cited by 398
Computational prediction of small-molecule catalysts
Houk, K. N., & Cheong, P. H.-Y. (2008) · Nature · doi:10.1038/nature07368 · Cited by 329
Self-citationMaley, S. M., Kwon, D.-H., Rollins, N., Stanley, J. C., Sydora, O. L., Bischof, S. M., & Ess, D. H. (2020) · Chemical Science · doi:10.1039/d0sc03552a · Cited by 81
Amedjkouh, M., & Brandberg, M. (2008) · Chemical Communications · doi:10.1039/b804142n · Cited by 54
Metadata
- Authors
- Mitsumori, S., Zhang, H., Ha-Yeon Cheong, P., Houk, K. N., Tanaka, F., & Barbas, C. F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-01-04
- Volume
- 128
- Issue
- 4
- Pages
- 1040-1041
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2107108994
- Cited by
- 305
- References
- 0
- FWCI
- 24.13
- Type
- journal article
- Language
- en
- Open access
- green
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- Mitsumori, S., Zhang, H., Ha-Yeon Cheong, P., Houk, K. N., Tanaka, F., & Barbas, C. F. (2006). Direct Asymmetric anti-Mannich-Type Reactions Catalyzed by a Designed Amino Acid. Journal of the American Chemical Society. https://doi.org/10.1021/ja056984f
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