A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis
Name
Angew Chem Int Ed - 2022 - Levi Knippel - A General Strategy for the Asymmetric Preparation of ‐Stereogenic Allyl Silanes .pdf
Description
Published version
Size
5 MB
Format
Adobe PDF
Checksum (MD5)
e69a6af2440ab84135faca3ed98982b1
Author(s)
Levi Knippel, James
Ni, Anton Z
Schuppe, Alexander W
Buchwald, Stephen L
Date Issued
2022
Journal
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
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-NonCommercial-NoDerivs License
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1002/ANIE.202212630
