Nickel-Catalyzed Organozinc-Promoted Carbocyclizations of Electron-Deficient Alkenes with Tethered Unsaturation
Publication type: Journal Article
Publication date: 1997-05-01
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
A nickel-catalyzed method for cyclizations of electron-deficient alkenes with tethered unsaturation in the presence of organozincs was developed. Considerable flexibility in the structure of each reactive component was observed. Enones, alkylidene malonates, unsaturated β-ketoesters, and nitroalkenes participated as the electron-deficient alkene; alkynes, enones, 1,3-dienes, and aldehydes participated as the tethered unsaturation; and a variety of sp2 and sp3-hybridized organozincs, including those that possess β-hydrogens, participated as the nucleophilic component. Substrate structure, organozinc structure, and ligand structure all played a significant role in determining product selectivities. Of particular synthetic significance was the opportunity to prepare either E or Z tri- or tetrasubstituted alkenes from a common alkyne. A discussion of probable mechanisms is provided.
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122
Total citations:
122
Citations from 2024:
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(5%)
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GOST
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Montgomery J., Oblinger E., Savchenko A. V. Nickel-Catalyzed Organozinc-Promoted Carbocyclizations of Electron-Deficient Alkenes with Tethered Unsaturation // Journal of the American Chemical Society. 1997. Vol. 119. No. 21. pp. 4911-4920.
GOST all authors (up to 50)
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Montgomery J., Oblinger E., Savchenko A. V. Nickel-Catalyzed Organozinc-Promoted Carbocyclizations of Electron-Deficient Alkenes with Tethered Unsaturation // Journal of the American Chemical Society. 1997. Vol. 119. No. 21. pp. 4911-4920.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja9702125
UR - https://doi.org/10.1021/ja9702125
TI - Nickel-Catalyzed Organozinc-Promoted Carbocyclizations of Electron-Deficient Alkenes with Tethered Unsaturation
T2 - Journal of the American Chemical Society
AU - Montgomery, John
AU - Oblinger, Eric
AU - Savchenko, Alexey V
PY - 1997
DA - 1997/05/01
PB - American Chemical Society (ACS)
SP - 4911-4920
IS - 21
VL - 119
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{1997_Montgomery,
author = {John Montgomery and Eric Oblinger and Alexey V Savchenko},
title = {Nickel-Catalyzed Organozinc-Promoted Carbocyclizations of Electron-Deficient Alkenes with Tethered Unsaturation},
journal = {Journal of the American Chemical Society},
year = {1997},
volume = {119},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/ja9702125},
number = {21},
pages = {4911--4920},
doi = {10.1021/ja9702125}
}
Cite this
MLA
Copy
Montgomery, John, et al. “Nickel-Catalyzed Organozinc-Promoted Carbocyclizations of Electron-Deficient Alkenes with Tethered Unsaturation.” Journal of the American Chemical Society, vol. 119, no. 21, May. 1997, pp. 4911-4920. https://doi.org/10.1021/ja9702125.