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Showing 1 to 5 of 5 for “"N-methyliminodiacetic acid"”.
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Iterative cross-coupling with MIDA boronates
… cross-coupling (ICC) of bifunctional haloboronic acid building blocks. Realizing a general ICC approach in the context of small molecule synthesis required the discovery of a ligand with the capacity to attenuate the reactivity of boronic acids under Suzuki-Miyaura cross-coupling (SMC) conditions …
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A small molecule synthesizer
… (ICC) strategy enabled by the capacity of N-methyliminodiacetic acid (MIDA) to reversibly attenuate the reactivity of a boronic acid. MIDA boronates are generally crystalline free-flowing solids and are stable to bench-top storage. Furthermore, it has been discovered that they are universally …
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Slow-release cross-coupling and an advanced method for β-glycosylation: methods stimulated by amphotericin B
… cross-coupling protocol was developed whereby N-methyliminodiacetic acid (MIDA) boronates can be used directly in Suzuki-Miyaura cross-coupling (SMC) reactions, enabling air-stable MIDA boronates to act as surrogates for boronic acids. Additionally, conditions were identified under which MIDA …
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Part I: synthesis and cross-coupling of the C1-C12 primary organoborane building block of amphotericin B; Part II: site- and stereoretentive cross-coupling of unactivated secondary boronic acids inspired by amphotericin B
… limit, a collection of off-the-shelf boronic acid-based building blocks having all of the required functional groups pre-installed in the correct oxidation states and with the desired stereochemical relationships are readily assembled using only a single cross-coupling reaction repeatedly. …
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Total synthesis and study of the antilipoperoxidant peridinin, synthesis of versatile MIDA boronate building blocks, and a general strategy for the synthesis of polyenes
Taking advantage of the inherent modularity present in the majority of small molecule natural products, we envision that a building block based approach involving the iterative cross-coupling of MIDA boronate containing molecules can be a universal platform for the preparation of small molecules. …