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Fernández, E.: 2020 Science of Synthesis, 2019/6: Advances in Organoboron Chemistry towards Organic Synthesis DOI: 10.1055/sos-SD-230-00065
Advances in Organoboron Chemistry towards Organic Synthesis

6 Borylation of Carbonyl and Imine Groups

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Editor: Fernández, E.

Authors: Aggarwal, V. K.; Ahmed, E.-A. M. A. ; Aiken, S. G.; Bateman, J. M.; Boldrini, C.; Bose, S. K. ; Carbó, J. J. ; Cho, H. Y.; Clark, T. B. ; Fernández, E.; Fu, Y. ; Geetharani, K. ; Gong, T.-J. ; Ito, H. ; Kitanosono, T.; Kobayashi, S.; Kubota, K. ; Maseras, F. ; Ohmiya, H. ; Pineschi, M.; Ping, Y.; Sawamura, M. ; Wang, J. ; Wang, Y.-F.; Wu, C.; Xu, L. ; Yoshida, H. ; Zhang, F.-L.

Title: Advances in Organoboron Chemistry towards Organic Synthesis

Print ISBN: 9783132429710; Online ISBN: 9783132429758; Book DOI: 10.1055/b-006-164898

2020 © 2020. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner (Editor-in-Chief), A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

The nucleophilic borylation of carbonyl groups and imines provides α-oxy and α-amino boronate esters, respectively, under a variety of metal-catalyzed and metal-free reaction conditions. The resulting boronate esters, which can be accessed in high enantiopurity, have been utilized in a variety of transformations based on the reactivity of the carbon–boron bond. For α-oxy boronate esters, the oxygen or boron is often protected for increased stability. Formation of carbon–carbon bonds by homologation reactions and Suzuki–Miyaura-type coupling reactions provides advanced intermediates in synthesis. A variety of methods have been developed for the asymmetric synthesis of α-amino boronate esters, a key precursor to the α-amino boronic acid pharmacophore. Application of these methods to the synthesis of bortezomib and a precursor to (R)-cetirizine have been demonstrated.

Key words

borylation - aldehydes - ketones - imines - homogeneous catalysis - asymmetric catalysis - organocatalysis - homologation - 1,2-metalate rearrangement - Suzuki–Miyaura coupling - bortezomib - cetirizine - α-hydroxy boronate esters - α-amino boronate esters - trifluoroborate salts
 
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