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Updated: Nov 30, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Effective Enantioselective Recognition by Chiral Amino-Phosphonium Salts*
Prabhakaran Rajasekar1, Cavya Jose1, Meghamala Sarkar1
1Department of Chemistry, Indian Institute of Science Education and Research, Pune, Dr. Homi Bhabha Road, Pune, 411008, India.
Abstract:
The research on chiral recognition and selection is not only fundamental in deciding the mystery of homochirality, but also informative in terms of substrate recognition in biological processes and asymmetric catalysis. We report an enantiomeric pair of phosphonium salts having chiral (R and S) amino substituents that are utilized towards the enantioselective recognition of a variety of chiral compounds having functional groups, such as carboxylic acid, amine, and alcohol. These simple phosphonium salts are found to exhibit a high enantiomeric discrimination for 1-cyclohexylethylamine (CY). A remarkable guest selectivity (ξ) value of 5.3×108 is achieved for the enantiomer of R-CY over S-CY by using the R-isomer of the phosphonium salt. Such high binding selectivities and discrimination capabilities is attributed to multiple non-covalent interactions between the host and guest molecules as inferred from the DFT optimized structures of the host-guest pairs.
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