Abstract
(Chemical Equation Presented) A chiral diaryl prolinol silyl ether organocatalyst with an acidis used for the direct catalytic asymmetric Mannich reaction of acetaldehyde and imines. N-Benzoyl-, N-tert-butoxycarbonyl-, and N-toluene-4-sulfonylimines can be employed to produce synthetically useful β-amino aldehydes in goodyield s andwith excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically.
| Original language | English |
|---|---|
| Pages (from-to) | 9053-9058 |
| Number of pages | 6 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 47 |
| Issue number | 47 |
| DOIs | |
| Publication status | Published - 2008 Nov 10 |
| Externally published | Yes |
Keywords
- Acetaldehyde
- Asymmetric catalysis
- Imines
- Mannich reactions
- Organocatalysis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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Cite this
Hayashi, Y., Okano, T., Itoh, T., Urushima, T., Ishikawa, H., & Uchimaru, T. (2008). Direct organocatalytic Mannich reaction of acetaldehyde: An improved catalyst and mechanistic insight from a computational study. Angewandte Chemie - International Edition, 47(47), 9053-9058. https://doi.org/10.1002/anie.200802073