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Showing 1 to 9 of 9 for “"MIDA boronate"”.
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Design of a second generation MIDA boronate: iterating c(sp3) based Suzuki cross couplings
… require conditions which hydrolyze MIDA boronates (aqueous base, high heat, strong base, etc.). In this thesis I describe the development of a second generation iminodiacetic acid ligand for boronic acids which is refractory to hydrolysis and has enabled the first examples of …
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Expansion of the iterative cross-coupling synthesis strategy through Csp3 halide cross-coupling, Mida boronate synthesis, and chan-lam couplings
… We also report a new method for the synthesis of MIDA boronates which are sensitive to current methods. Finally, we report the extension of the entire iterative cross coupling platform to the Chan-Lam coupling to form carbon-heteroatom bonds.
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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
… involving the iterative cross-coupling of MIDA boronate containing molecules can be a universal platform for the preparation of small molecules. Guided by this strategy we completed an efficient, flexible, and fully stereocontrolled synthesis of the carotenoid natural product peridinin. …
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A small molecule synthesizer
… 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 amenable to …
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Slow-release cross-coupling and an advanced method for β-glycosylation: methods stimulated by amphotericin B
… 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 boronates could be slowly …
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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
… to make Csp3 organo-N-methyliminodiacetic acid (MIDA) boronate building blocks that are indefinitely bench-top stable. Additionally, inspired by our ongoing total synthesis of AmB, I discovered a solution to the long-standing problem of site-, and stereoretentive cross-coupling of unactivated …
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Semisynthesis of amphotericin B and its derivatives via iterative cross-coupling
… cross-coupling of bifunctional polyenyl MIDA boronate building blocks. This methodology was taken on to complete efficient total syntheses of all-trans-retinal, β-parinaric acid, and one half of AmB. In order to validate this iterative cross-coupling methodology as an effective endgame …
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Iterative cross-coupling with MIDA boronates
… Towards this end, N-methyliminodiacetic acid (MIDA) was discovered to be such a ligand, enabling an approach by which the reactivity of boronic acids is modulated via rehybridization of the boron center. Further, MIDA boronates, which result from the condensation of MIDA with boronic acids, …
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Expansion and automation of iterative cross-coupling: total synthesis of synechoxanthin and development of a small molecule synthesizer
Item withdrawn by Mark Zulauf (zulauf@illinois.edu) on 2014-04-15T20:00:36Z Item was in collections: University of Illinois Theses & Dissertations (ID: 1) No. of bitstreams: 1 Sisco_Seiko.pdf: 39731093 bytes, checksum: c5a677f96924a2150cc9bc68dfe0cc54 (MD5)