A new chiral primary–tertiary diamine-Brønsted acid salt organocatalyst for the highly enantioselective direct anti-aldol and syn-Mannich reactions

A new chiral primary–tertiary diamine-Brønsted acid salt organocatalyst for the highly... A new primary–tertiary diamine catalyst is easily prepared in a few steps from inexpensive, commercially available, enantiopure materials. This organocatalyst can be effective catalyzed the direct asymmetric aldol and Mannich reactions. The anti-aldol products can be obtained with up to a 99:1 anti/syn ratio and >98 % ee, while the syn-Mannich products could be obtained with up to a 99:1 syn/anti ratio and >99 % ee. Catalyst 1c can be used efficiently on a large scale with the enantioselectivities of the anti-aldol and syn-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

A new chiral primary–tertiary diamine-Brønsted acid salt organocatalyst for the highly enantioselective direct anti-aldol and syn-Mannich reactions

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Publisher
Springer Journals
Copyright
Copyright © 2012 by Springer Science+Business Media B.V.
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-012-0667-x
Publisher site
See Article on Publisher Site

Abstract

A new primary–tertiary diamine catalyst is easily prepared in a few steps from inexpensive, commercially available, enantiopure materials. This organocatalyst can be effective catalyzed the direct asymmetric aldol and Mannich reactions. The anti-aldol products can be obtained with up to a 99:1 anti/syn ratio and >98 % ee, while the syn-Mannich products could be obtained with up to a 99:1 syn/anti ratio and >99 % ee. Catalyst 1c can be used efficiently on a large scale with the enantioselectivities of the anti-aldol and syn-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jul 3, 2012

References

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