Abstract
The application of the most representative and up-to-date examples of homogeneous asymmetric organocatalysis to the synthesis of molecules of interest in medicinal chemistry is reported. The use of different types of organocatalysts operative via noncovalent and covalent interactions is critically reviewed and the possibility of running some of these reactions on large or industrial scale is described. A comparison between the organo- and metal-catalysed methodologies is offered in several cases, thus highlighting the merits and drawbacks of these two complementary approaches to the obtainment of very popular on market drugs or of related key scaffolds.
Highlights
Over the past ten years, the field of enantioselective organocatalysis has had a significant impact on chemical synthesis [1, 2]
Asymmetric organocatalysis is recognized [3] as an independent synthetic tool besides asymmetric metallic catalysis and enzymatic catalysis for the synthesis of chiral organic molecules
Several groups have made a remarkable effort to show the great applicability of organocatalysts to the total synthesis of bioactive natural products [18] and of drugs [19] most of them currently available in the market such as oseltamivir, warfarin, paroxetine, baclofen, and maraviroc
Summary
Over the past ten years, the field of enantioselective organocatalysis has had a significant impact on chemical synthesis [1, 2]. Organocatalysts turn out to be favourable when used in catalytic cascade reactions because they allow distinct modes of activation, which can often be combined [16, 17] Despite their great development, the application of organocatalytic methodologies to the synthesis of active compounds in medicinal chemistry in the past years has rarely been reported. Several groups have made a remarkable effort to show the great applicability of organocatalysts to the total synthesis of bioactive natural products [18] and of drugs [19] most of them currently available in the market such as oseltamivir, warfarin, paroxetine, baclofen, and maraviroc These efforts mainly focused on the removal of barriers for scale-up by addressing issues such as catalyst loading, product inhibition, substrate scope, and bulk availability of designer catalysts which have drawn the attention of the companies [20, 21] that have begun to incorporate organocatalysis as a synthetic tool in some industrial scale processes [22, 23]. A comparison between organoand metal-catalysed methodologies aimed at the obtainment of the same medicinal targets will be reported and a few interesting industrial examples of the use of organocatalysis in medicinal chemistry taken from the literature will be discussed as well
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
