This work was partially supported by the Toray Science Foundation, and a Grant-in-Aid for Scientific Research from MEXT. We thank Tsukuba Advanced Computing Center (TACC) for the provision of computational facilities.
Direct Organocatalytic Mannich Reaction of Acetaldehyde: An Improved Catalyst and Mechanistic Insight from a Computational Study†
Article first published online: 16 OCT 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 47, pages 9053–9058, November 10, 2008
How to Cite
Hayashi, Y., Okano, T., Itoh, T., Urushima, T., Ishikawa, H. and Uchimaru, T. (2008), Direct Organocatalytic Mannich Reaction of Acetaldehyde: An Improved Catalyst and Mechanistic Insight from a Computational Study. Angew. Chem. Int. Ed., 47: 9053–9058. doi: 10.1002/anie.200802073
- Issue published online: 5 NOV 2008
- Article first published online: 16 OCT 2008
- Manuscript Revised: 28 AUG 2008
- Manuscript Received: 2 MAY 2008
- asymmetric catalysis;
- Mannich reactions;
A chiral diaryl prolinol silyl ether organocatalyst with an acid is 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 good yields and with excellent enantioselectivity (see scheme). The reaction mechanism was investigated quantum-mechanically.