Aminoboronic acids and their derivatives are particularly useful as drugs, probes and synthons. Recent developments in their synthesis are highlighted.
The most common types of acylboranes
are acyltrifluoroborates,
acyl MIDA-boronates, and monofluoroacylboronates. Because of the increasing
importance of these compounds in the past decade, we highlight the
recently reported synthetic strategies to access acylboranes. In addition,
an expanding array of their applications has been discovered, based
on either the ability of acylboranes to enter rapid amide-forming
ligations or the retained ketone-like character of the carbonyl group.
Therefore, we also describe ground-breaking achievements where acylboranes
were successfully put to use, such as their utility in biochemical,
material, and medicinal sciences.
A series of structurally diverse benzyl protected trifluoroborate‐ammoniums were prepared in good to high yields by an efficient hydrogenation of corresponding trifluoroborate‐iminiums using Crabtree's catalyst. Subsequent N‐ and B‐deprotections were demonstrated on selected examples to provide several α‐aminoboronic acids. Preliminary experiments on asymmetric version of the reaction indicated a correlation between E/Z‐ratio in the trifluoroborate‐iminium substrate and enantioselectivity. The broad scope, operational simplicity and efficiency of the presented method imply its high potential for a facile access to libraries of α‐aminoboronic acid derivatives that can be used in medicinal chemistry applications and beyond.
This work describes the first preparation and application of primary trifluoroborate‐iminiums (pTIMs) as new, easily accessible and valuable class of organoboron derivatives. An array of structurally diverse pTIMs was prepared...
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