Enantio- and Regioconvergent Nickel-Catalyzed Allylic Substitution of Racemic α- or γ-Silylated Allylic Bromides with Benzylzinc Reagents
Publication type: Journal Article
Publication date: 2022-07-01
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
35776983
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An enantio- and regioconvergent nickel-catalyzed benzylation of racemic silylated allylic electrophiles with benzylzinc nucleophiles is reported. The key feature of this method is that the homocoupling pathways of both the nucleophile and the electrophile are minimized. A diverse set of electronically modified benzylzinc reagents was tolerated. The vinylsilane products with allylic stereocenters were formed in moderate to high yields with high enantioselectivities. The regioconvergence is the result of the steering effect of the silyl group.
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16
Total citations:
16
Citations from 2024:
10
(62.5%)
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GOST
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Kranidiotis Hisatomi N., Oestreich M. Enantio- and Regioconvergent Nickel-Catalyzed Allylic Substitution of Racemic α- or γ-Silylated Allylic Bromides with Benzylzinc Reagents // Organic Letters. 2022. Vol. 24. No. 27. pp. 4987-4991.
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Kranidiotis Hisatomi N., Oestreich M. Enantio- and Regioconvergent Nickel-Catalyzed Allylic Substitution of Racemic α- or γ-Silylated Allylic Bromides with Benzylzinc Reagents // Organic Letters. 2022. Vol. 24. No. 27. pp. 4987-4991.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.2c02076
UR - https://doi.org/10.1021/acs.orglett.2c02076
TI - Enantio- and Regioconvergent Nickel-Catalyzed Allylic Substitution of Racemic α- or γ-Silylated Allylic Bromides with Benzylzinc Reagents
T2 - Organic Letters
AU - Kranidiotis Hisatomi, Nektarios
AU - Oestreich, Martin
PY - 2022
DA - 2022/07/01
PB - American Chemical Society (ACS)
SP - 4987-4991
IS - 27
VL - 24
PMID - 35776983
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2022_Kranidiotis Hisatomi,
author = {Nektarios Kranidiotis Hisatomi and Martin Oestreich},
title = {Enantio- and Regioconvergent Nickel-Catalyzed Allylic Substitution of Racemic α- or γ-Silylated Allylic Bromides with Benzylzinc Reagents},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.orglett.2c02076},
number = {27},
pages = {4987--4991},
doi = {10.1021/acs.orglett.2c02076}
}
Cite this
MLA
Copy
Kranidiotis Hisatomi, Nektarios, and Martin Oestreich. “Enantio- and Regioconvergent Nickel-Catalyzed Allylic Substitution of Racemic α- or γ-Silylated Allylic Bromides with Benzylzinc Reagents.” Organic Letters, vol. 24, no. 27, Jul. 2022, pp. 4987-4991. https://doi.org/10.1021/acs.orglett.2c02076.