Use of Triethylsilane for Directed Enantioselective Reduction of Olefines: Synthesis of Pyrazino[2,1-c][1,4]oxazine-6,9-diones with Full Control of the Absolute Configuration
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F18%3A73591003" target="_blank" >RIV/61989592:15110/18:73591003 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/18:73591003
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201701553" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201701553</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201701553" target="_blank" >10.1002/ejoc.201701553</a>
Alternative languages
Result language
angličtina
Original language name
Use of Triethylsilane for Directed Enantioselective Reduction of Olefines: Synthesis of Pyrazino[2,1-c][1,4]oxazine-6,9-diones with Full Control of the Absolute Configuration
Original language description
Herein, we report the use of triethylsilane for the synthesis of hexahydropyrazino[2,1-c][1,4]oxazine-6,9-diones with full control of three stereocenters. Unsaturated tetrahydropyrazino-oxazine-diones were prepared according to a previously reported procedure and were reacted with triethylsilane-trifluoroacetic acid. The stereoselectivity of the reduction was completely dependent on the overall conformation of the oxazine scaffold, which was a consequence of the C9 configuration of the starting material. The results prove that triethylsilane can be used for directed enantioselective syntheses of single or fused morpholine-based heterocycles.
Czech name
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Czech description
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Classification
Type
J<sub>ost</sub> - Miscellaneous article in a specialist periodical
CEP classification
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OECD FORD branch
10401 - Organic chemistry
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>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2018
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 (online)
ISSN
1099-0690
e-ISSN
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Volume of the periodical
2018
Issue of the periodical within the volume
4
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
564-570
UT code for WoS article
000423772600018
EID of the result in the Scopus database
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