Highly enantioselective aldol reactions catalyzed by reusable upper rim-functionalized calix[4]arene-based L-proline organocatalyst in aqueous conditions

A series of upper rim-functionalized calix[4]arene-based L-Proline derivatives have been synthesized and employed for the enantioselective aldol reactions between cyclic ketones and aromatic aldehydes in the presence of water. Good to excellent yields (up to 96%), enantioselectivities (up to 99% ee), as well as diastereoselectivities (up to 99:1 dr) were obtained under the optimal reaction conditions. Detailed experiments clearly showed that the hydrophobic calixarene platform not only contributed to the good reactivities and enantioselectivities, but also exhibited size-selective catalysis function. Moreover, the organocatalyst can be readily recovered and reused for several runs without significant loss in its enantioselectivity. (C) 2016 Elsevier Ltd. All rights reserved.