A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis
Author(s)
Levi Knippel, James; Ni, Anton Z; Schuppe, Alexander W; Buchwald, Stephen L
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α-Stereogenic allyl metalloids are versatile synthetic intermediates which can undergo various stereocontrolled transformations. Most existing methods to prepare α-stereogenic allyl metalloids involve multi-step sequences that curtail the number of compatible substrates and are limited to the synthesis of boronates. Here, we report a general method for the enantioselective preparation of α-stereogenic allyl metalloids utilizing dual CuH- and Pd-catalysis. This approach leverages a stereoretentive Cu-to-Pd transmetalation of an in situ generated alkyl copper species to allow access to enantioenriched allyl silanes, germanes, and boronate esters with broad functional group compatibility.
Date issued
2022Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Angewandte Chemie - International Edition
Publisher
Wiley
Citation
Levi Knippel, James, Ni, Anton Z, Schuppe, Alexander W and Buchwald, Stephen L. 2022. "A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis." Angewandte Chemie - International Edition, 61 (47).
Version: Final published version