Abstract
Enantiomerically pure tailor-made amino acids are in extremely high demand in nearly every sector of the health-related industries. In particular, the rapidly growing number of amino-acid-based pharmaceuticals calls for the development of advanced synthetic approaches featuring practicality and commercial viability. Here we provide a brief summary of the development of axially chiral tridentate Hamari ligands and their application for general asymmetric synthesis of various structural types of amino acids. The methodological diversity includes: dynamic kinetic resolution and (S)-/(R)-interconversion of unprotected amino acids and homologation of nucleophilic glycine equivalents via alkyl halide alkylation reactions as well as multiple-step transformations allowing preparation of polyfunctional and cyclic derivatives. The practicality of these methods is critically discussed.
Highlights
Amino acids (AAs) are among a few fundamental “building blocks of life” and have played a significant role in drug discovery from the earliest days of modern pharmaceutical science
We provide a brief summary of the development of axially chiral tridentate Hamari ligands and their application for general asymmetric synthesis of various structural types of amino acids
In this mini-review, we would like to acquaint the readers with the most recent developments in the field dealing with the design of new chiral nucleophilic glycine equivalents as versatile reagents for general asymmetric synthesis of tailor-made AAs
Summary
Amino acids (AAs) are among a few fundamental “building blocks of life” and have played a significant role in drug discovery from the earliest days of modern pharmaceutical science. Tailor-made AAs are indispensable components of modern medicinal chemistry and are becoming increasingly prominent in new pharmaceuticals and medical formulations. The growing recognition of peptides and peptidomimetics as preferred drugs advocates for the growing role of tailor-made AAs in the modern pharmaceutical industry.[1] The synthesis of AAs is a welldeveloped discipline offering a plethora of various methodological approaches. We focus on the chiral Hamari ligands and glycine derivatives, as the most promising reagents for large-scale practical solutions
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