Abstract
Linear amino acids covalently supported on graphene sheet were employed as catalysts for asymmetric aldol reactions between cyclohexanone and aldehydes (aliphatic and/or aromatic) in a batch type reactor in the presence of water. The reactions were found to exhibit high yield as well as excellent ee value. Additionally, the catalysts were found to be truly heterogeneous and eco-friendly.
Highlights
Linear amino acids have been extensively investigated as effective homogenous catalysts in asymmetric aldol reactions between ketone and aldehyde in the presence of polar solvents [1]-[3]
We have been successful in developing a new pathway for the immobilization of linear amino acids covalently, on graphene sheet
Of the intermediate of the enamine catalytic cycle. These results provide clear evidence that acyclic amino acids covalently immobilized on graphene are remarkable chiral organo-catalysts, capable of catalyzing the direct asymmetric aldol reaction with excellent reactivity and stereoselectivity
Summary
Linear amino acids have been extensively investigated as effective homogenous catalysts in asymmetric aldol reactions between ketone and aldehyde in the presence of polar solvents [1]-[3]. To answer the issues inherent to the use of amino acids in homogeneous systems, researchers intensively exploited suitable alternatives to replace these environmentally malignant systems [5]. In this scenario, immobilization of amino acids on a suitable support could simplify the separation of products, and facilitate the recovery and reusability of the catalysts [6]. The recovery of the catalyst without loss of its activity and its subsequent re-usability is an important finding in both studies These studies motivated us to investigate the efficiency and capability of covalently immobilized linear amino acids on graphene sheet for asymmetric aldol reactions between cyclohexanone and aromatic and aliphatic aldehydes under eco-friendly reaction conditions
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