A new chiral primary–tertiary diamine-Brønsted acid
salt organocatalyst for the highly enantioselective direct
anti-aldol and syn-Mannich reactions
Received: 21 April 2012 / Accepted: 28 May 2012 / Published online: 3 July 2012
Ó Springer Science+Business Media B.V. 2012
Abstract A new primary–tertiary diamine catalyst is easily prepared in a few steps
from inexpensive, commercially available, enantiopure materials. This organocata-
lyst 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 enanti-
oselectivities of the anti-aldol and syn-Mannich reactions being maintained at the
same level, which offers a great possibility for application in industry.
Keywords Cyclohexyldiamine Á Aldol reactions Á Mannich reactions Á
Large scale Á Stoichiometric
The development of stereoselective and enantioselective aldol and Mannich
reactions have become interesting and challenging topics in modern organic and
medicinal chemistry [1–3], because the resulting chiral b-hydroxy ketones and 1,2-
amino alcohols belong to an extremely important class of biological compounds.
Electronic supplementary material The online version of this article (doi:10.1007/
s11164-012-0667-x) contains supplementary material, which is available to authorized users.
G. Chen Á X. Fu (&) Á C. Wu Á C. Li
College of Chemistry and Chemical Engineering, Research Institute of Applied Chemistry
Southwest University, The Key Laboratory of Applied Chemistry of Chongqing Municipality,
Chongqing Unis Chemical Co, Ltd, Chongqing 402161, China
Res Chem Intermed (2013) 39:1069–1087