Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes
Menghua Xu
1
,
Qingbin Lu
1
,
Baihui Gong
1
,
Wenqing Ti
1
,
Aijun Lin
1
,
Hequan Yao
1
,
Shang Gao
1
Publication type: Journal Article
Publication date: 2023-09-18
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
37667513
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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Metrics
22
Total citations:
22
Citations from 2024:
19
(86.36%)
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GOST
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Xu M. et al. Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes // Angewandte Chemie - International Edition. 2023. Vol. 62. No. 44.
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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.
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RIS
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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 -
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BibTex (up to 50 authors)
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@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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