A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis

Publication typeJournal Article
Publication date2022-09-22
scimago Q1
wos Q1
SJR5.550
CiteScore27.6
Impact factor16.9
ISSN14337851, 15213773
General Chemistry
Catalysis
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 stereospecific 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.
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Knippel J. L. et al. 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. 2022. Vol. 61. No. 47.
GOST all authors (up to 50) Copy
Knippel J. L., Ni A. Z., Schuppe A. W., Buchwald S. L. 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. 2022. Vol. 61. No. 47.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/anie.202212630
UR - https://doi.org/10.1002/anie.202212630
TI - A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis
T2 - Angewandte Chemie - International Edition
AU - Knippel, James Levi
AU - Ni, Anton Z
AU - Schuppe, Alexander W
AU - Buchwald, Stephen L.
PY - 2022
DA - 2022/09/22
PB - Wiley
IS - 47
VL - 61
PMID - 36137941
SN - 1433-7851
SN - 1521-3773
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Knippel,
author = {James Levi Knippel and Anton Z Ni and Alexander W Schuppe and Stephen L. Buchwald},
title = {A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐ and Palladium‐Catalysis},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {61},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/anie.202212630},
number = {47},
doi = {10.1002/anie.202212630}
}