Regio- and stereoselective cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzoylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to methyl methacrylate
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F11%3A39892208" target="_blank" >RIV/00216275:25310/11:39892208 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.tet.2011.09.140" target="_blank" >http://dx.doi.org/10.1016/j.tet.2011.09.140</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2011.09.140" target="_blank" >10.1016/j.tet.2011.09.140</a>
Alternative languages
Result language
angličtina
Original language name
Regio- and stereoselective cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzoylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to methyl methacrylate
Original language description
[3+2] Cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzoylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides 1a-e to methyl methacrylate gave the 1-CO2Me regioisomers 3/3?, exclusively, in 1-67% yields. Stereocontrol was dependent on the ortho-substituents at the 1?-aryl group in dipole 1: ortho-unsubstituted dipoles 1a-c gave the major (1R*,3R*,5R*,6R*)-isomers 3a-c, whilst ortho-disubstituted dipoles gave the major (1R*,3S*,5R*,6R*)-isomers 3?d,e. The structures of cycloadducts were determined by NMRand X-ray diffraction.
Czech name
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Czech description
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Classification
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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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2011
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Tetrahedron
ISSN
0040-4020
e-ISSN
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Volume of the periodical
67
Issue of the periodical within the volume
50
Country of publishing house
GB - UNITED KINGDOM
Number of pages
7
Pages from-to
9729-9735
UT code for WoS article
000297485800010
EID of the result in the Scopus database
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