Synthesis of aminoboronic acid derivatives: an update on recent advances

Abstract

Aminoboronic acids and their derivatives are particularly useful as drugs, probes and synthons. Recent developments in their synthesis are highlighted.

Catalytic Approach to Diverse α‐Aminoboronic Acid Derivatives by Iridium‐Catalyzed Hydrogenation of Trifluoroborate‐Iminiums

“…Herein, we report a novel catalytic hydrogenation of N ‐benzyl protected TIMs to TAMs that can be N ‐deprotected under catalytic conditions (Scheme 1). The removal of benzyl and trifluoroborate protecting groups in TAMs would give an access to α‐aminoboronic acids, key elements in the synthesis of aminoboronic acid containing peptides [1b] …”

Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry

“…As might be anticipated from Figure 1, two boron-based chemotypes are currently predominant in drug discovery: i) aminoboronic acids or their derivatives (typically chiral); ii) benzoxaboroles-cyclic arylboronates that are beyond the scope of this review. Recently, αand β-aminoboronic acids and their derivatives were surveyed comprehensively; [21][22][23] a number of more general reviews on organoboron compounds in medicinal chemistry were also published. [2,[11][12][13][14][15][16][17][18] Therefore, we shall limit further discussion by overview of recent approaches to the synthesis of enantiopure α-aminoboronic acids or their derivatives.…”

Acyl metalloids: conformity and deviation from carbonyl reactivity

“…Alternatively, defluorination with SiCl 4 leads to the generation of α-aminoboronic acids 9, which are not easily prepared with current methodology. 27,28 The high propensity of KATs to form imines was utilized by Ito and coworkers in order to develop a new class of boronate luminophores (Scheme 3). 29 Specifically, KATs 10 were condensed with 2-hydrazinopyridines (11) and subjected to a BF 3 •Et 2 O mediated defluorocyclization between boron and the pyridine nitrogen.…”