Abstract
Abstractα‐Aminoalkylboronic acids display a distinct role in medicinal chemistry, and their utility has been demonstrated by the successful commercialization of three drugs: bortezomib, ixazomib, and vaborbactam. Just as α‐aminoalkylboronic acids are a bioisostere of α‐amino acids, β‐aminoalkylboronates are a bona fide bioisostere of β‐amino acids, thus they also hold promising potential in drug discovery. Moreover, β‐aminoalkylboronates are versatile synthetic intermediates that are amenable to many of the established C−B bond derivatization reactions of chiral optically enriched alkylboronates, leading to the stereocontrolled preparation of valued classes of products such as β‐amino alcohols, 1,2‐diamines, and hemiboronic acid heterocycles. In addition, β‐aminoalkylboronates were shown to act as catalysts in certain organic reactions. This review presents an overview of the strengths and limitations of current preparative methods to access β‐aminoalkylboronic acid derivatives stereoselectively with various substitution patterns. Strategically, several disconnections can be exploited to establish both functional groups. Some of the key methods include the classical Matteson asymmetric homologation chemistry, transition metal‐catalyzed aminoboration of alkenes and formal hydroboration of enamine derivatives, nucleophilic additions of boryl‐substituted carbanions onto N‐functionalized imines, borylative ring openings of aziridines, and functionalization of alpha‐boryl aldehydes.magnified image
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: 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.