Substrate Control in the Gold(I)-Catalyzed Cyclization of beta-Propargylamino Acrylic Esters and Further Transformations of the Resultant Dihydropyridines

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10328135" target="_blank" >RIV/00216208:11310/16:10328135 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11160/16:10328135
Result on the web
<a href="http://onlinelibrary.wiley.com/doi/10.1002/adsc.201600412/full" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/adsc.201600412/full</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.201600412" target="_blank" >10.1002/adsc.201600412</a>

Result language
angličtina
Original language name
Substrate Control in the Gold(I)-Catalyzed Cyclization of beta-Propargylamino Acrylic Esters and Further Transformations of the Resultant Dihydropyridines
Original language description
N-Protected beta-propargylamino acrylic esters with a push-pull olefinic bond afforded good to high yields of dihydropyridines upon treatment with 5% tris(2-furyl)phosphine-gold(I) chloride/silver(I) tetrafluoroborate [(TFP)AuCl/AgBF4] in anhydrous benzene. Carbamate and sulfonyl groups were employed for nitrogen protection. On a model enyne, the p-methoxybenzenesulfonyl (MBS) group was found to be a better protective group than tosyl in terms of cyclization yield, and also the yield of elimination to the corresponding 2,3,4-trisubstituted pyridines. Boc-protected dihydropyridines underwent partial deprotection/oxidation under the cyclization conditions, which enabled a more straightforward, one-pot preparation of the corresponding pyridines. In another application, an appropriately substituted derivative protected as a stable methoxycarbamate was subjected to catalytic hydrogenation affording the known precursor of paroxetine. The chemoselectivity of enyne cyclization (dihydropyridine vs. pyrrole) is governed, among other factors, by C-3 substitution. Dihydropyridines were obtained as sole products regardless of the catalyst/conditions when C-3 was unsubstituted.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GA15-07332S" target="_blank" >GA15-07332S: Natural Lactones and Lactams: Towards Diverse Biological Activities through Purposeful Synthetic Manipulations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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