Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes

Publication typeJournal Article
Publication date2023-09-18
scimago Q1
wos Q1
SJR5.550
CiteScore27.6
Impact factor16.9
ISSN14337851, 15213773
General Chemistry
Catalysis
Abstract

We report herein a regiodivergent and enantioselective allyl addition to ketones with allenylsilanes through copper catalysis. With the combination of CuOAc, a Josiphos‐type bidentate phosphine ligand and PhSiH3, allyl addition to a variety of ketones furnishes branched products in excellent enantioselectivities. The regioselectivity is completely reversed by employing the P‐stereogenic ligand BenzP*, affording the linear products with excellent enantioselectivities and good Z‐selectivities. The linear Z‐product could be converted to E‐product via a catalytic geometric isomerization of the Z‐alkene group. The silyl group in the products could provide a handle for downstream elaboration.

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GOST Copy
Xu M. et al. Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes // Angewandte Chemie - International Edition. 2023. Vol. 62. No. 44.
GOST all authors (up to 50) Copy
Xu M., Lu Q., Gong B., Ti W., Lin A., Yao H., Gao S. Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes // Angewandte Chemie - International Edition. 2023. Vol. 62. No. 44.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1002/anie.202311540
UR - https://doi.org/10.1002/anie.202311540
TI - Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes
T2 - Angewandte Chemie - International Edition
AU - Xu, Menghua
AU - Lu, Qingbin
AU - Gong, Baihui
AU - Ti, Wenqing
AU - Lin, Aijun
AU - Yao, Hequan
AU - Gao, Shang
PY - 2023
DA - 2023/09/18
PB - Wiley
IS - 44
VL - 62
PMID - 37667513
SN - 1433-7851
SN - 1521-3773
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Xu,
author = {Menghua Xu and Qingbin Lu and Baihui Gong and Wenqing Ti and Aijun Lin and Hequan Yao and Shang Gao},
title = {Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes},
journal = {Angewandte Chemie - International Edition},
year = {2023},
volume = {62},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/anie.202311540},
number = {44},
doi = {10.1002/anie.202311540}
}
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