Ashokkumar Veeramanoharan, Chithiraikumar Chinnadurai, Siva Ayyanar
Supramolecular and Organometallic Chemistry Lab, School of Chemistry, Madurai Kamaraj University, Madurai-625 021, Tamil Nadu, India.
Org Biomol Chem. 2016 Oct 14;14(38):9021-32. doi: 10.1039/c6ob01558a. Epub 2016 Sep 7.
Novel binaphthyl-based chiral bifunctional organocatalysts were designed, synthesized and successfully applied to the asymmetric List-Lerner-Barbas aldol reaction in the presence of water. These organocatalysts were found to be effective catalysts for the reactions of symmetrical, unsymmetrical and cyclic ketones with different aldehydes to give the corresponding aldol products with higher yields (up to 98%) and very good ee's up to 99%. The catalytic system leads to higher yields and selectivities than the previously reported well-known proline based organocatalysts. In addition to the effect of solvent, additives, catalyst concentration, temperature and the substrate scope of the reactions were also investigated.
设计、合成了新型基于联萘的手性双功能有机催化剂，并成功将其应用于水存在下的不对称List-Lerner-Barbas羟醛反应。发现这些有机催化剂对于对称、不对称和环状酮与不同醛的反应是有效的催化剂，能以更高的产率（高达98%）和非常好的对映体过量值（高达99%）得到相应的羟醛产物。该催化体系比先前报道的著名的基于脯氨酸的有机催化剂能给出更高的产率和选择性。除了溶剂的影响外，还研究了添加剂、催化剂浓度、温度以及反应的底物范围。
