Enantioselective Organocatalytic Synthesis of Sulfur-Containing Spirocyclic Compounds
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F13%3A10191191" target="_blank" >RIV/00216208:11310/13:10191191 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201300931" target="_blank" >http://dx.doi.org/10.1002/ejoc.201300931</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201300931" target="_blank" >10.1002/ejoc.201300931</a>
Alternative languages
Result language
angličtina
Original language name
Enantioselective Organocatalytic Synthesis of Sulfur-Containing Spirocyclic Compounds
Original language description
Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described. In the first approach, benzothiophen-2-one and enals react in the presence of a secondary amine catalyst through a Michael/Michael/Aldol sequence to afford the final spiro-cyclohexene carbaldehydes in good yields (up to 68%) and with excellent selectivities [20:1 diastereomeric ratio (dr), up to 99%ee]. In the second approach, the double Michael addition of benzothiophen-2-one to aromatic dienones with primary amine catalysis produces the corresponding spiro-cyclohexanones in good yields (up to 76%) and with moderate-to-high selectivities (up to 12:1 dr, up to 90%ee). Moreover, the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocyclic adducts.
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
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
2013
Issue of the periodical within the volume
35
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
7979-7988
UT code for WoS article
000327775800018
EID of the result in the Scopus database
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