FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2270684480> ?p ?o ?g. }

• W2270684480 abstract "A general study is undertaken to examine the scope of the reductive ring opening of aziridine-2-carboxylates with samarium diiodide. The competition between C-C and C-N bond cleavage is examined as a function of the nature of the N-substituent of the aziridine, the nature of the substituent in the 3-position of the aziridine, and whether the substituent in the 3-position is in a cis or trans relationship with the carboxylate in the 2-position. The desired C-N bond cleavage leads to β-amino esters that are the predominant products for most aziridines with an N-activating group. However, C-C cleavage products are observed with an aryl group in the 3-position; this can be particularly pronounced with cis-aziridines where a nearly equal mixture of the two is observed. Exclusive formation of the C-N cleavage product is observed for all aziridines with the strongly N-activating p-toluene sulfonate group. Similarly high selectivity is observed for the 2-trimethylsilylethyl sulfonate group (SES), which is easier to remove. The utility of these methods is illustrated in the synthesis of protected forms of (R)-β(3)-DOPA and L-DOPA from the same aziridine, the former by SmI2-mediated reductive opening at C-2 and the latter by palladium-mediated reductive opening at C-3." @default.
• W2270684480 created "2016-06-24" @default.
• W2270684480 creator A5002363415 @default.
• W2270684480 creator A5064797131 @default.
• W2270684480 creator A5068068080 @default.
• W2270684480 date "2014-10-20" @default.
• W2270684480 modified "2023-09-29" @default.
• W2270684480 title "β-Amino Esters from the Reductive Ring Opening of Aziridine-2-carboxylates" @default.
• W2270684480 cites W1979801275 @default.
• W2270684480 cites W1985715194 @default.
• W2270684480 cites W1988486581 @default.
• W2270684480 cites W1999618865 @default.
• W2270684480 cites W2004996358 @default.
• W2270684480 cites W2008308257 @default.
• W2270684480 cites W2024810540 @default.
• W2270684480 cites W2027484306 @default.
• W2270684480 cites W2047497948 @default.
• W2270684480 cites W2059172388 @default.
• W2270684480 cites W2060152301 @default.
• W2270684480 cites W2072003934 @default.
• W2270684480 cites W2076995565 @default.
• W2270684480 cites W2080572255 @default.
• W2270684480 cites W2086480746 @default.
• W2270684480 cites W2088501206 @default.
• W2270684480 cites W2097614647 @default.
• W2270684480 cites W2097880985 @default.
• W2270684480 cites W2097981241 @default.
• W2270684480 cites W2106186782 @default.
• W2270684480 cites W2113161241 @default.
• W2270684480 cites W2129081889 @default.
• W2270684480 cites W2132228365 @default.
• W2270684480 cites W2143534082 @default.
• W2270684480 cites W2145954079 @default.
• W2270684480 cites W2148088350 @default.
• W2270684480 cites W2150377190 @default.
• W2270684480 cites W2150530305 @default.
• W2270684480 cites W2157087493 @default.
• W2270684480 cites W2164780036 @default.
• W2270684480 cites W2166857069 @default.
• W2270684480 cites W2313099135 @default.
• W2270684480 cites W2315122602 @default.
• W2270684480 cites W2324375440 @default.
• W2270684480 cites W2331526554 @default.
• W2270684480 cites W2478964621 @default.
• W2270684480 cites W2949620794 @default.
• W2270684480 cites W2949921933 @default.
• W2270684480 cites W2950206396 @default.
• W2270684480 cites W2950259028 @default.
• W2270684480 cites W2950335050 @default.
• W2270684480 cites W2950526068 @default.
• W2270684480 cites W2950597994 @default.
• W2270684480 cites W2950762657 @default.
• W2270684480 cites W2950935219 @default.
• W2270684480 cites W2952238764 @default.
• W2270684480 cites W2952849938 @default.
• W2270684480 cites W2953116453 @default.
• W2270684480 cites W2953146815 @default.
• W2270684480 cites W2953344646 @default.
• W2270684480 cites W4235639095 @default.
• W2270684480 doi "https://doi.org/10.1021/jo501694h" @default.
• W2270684480 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4227569" @default.
• W2270684480 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25329528" @default.
• W2270684480 hasPublicationYear "2014" @default.
• W2270684480 type Work @default.
• W2270684480 sameAs 2270684480 @default.
• W2270684480 citedByCount "7" @default.
• W2270684480 countsByYear W22706844802015 @default.
• W2270684480 countsByYear W22706844802018 @default.
• W2270684480 countsByYear W22706844802019 @default.
• W2270684480 crossrefType "journal-article" @default.
• W2270684480 hasAuthorship W2270684480A5002363415 @default.
• W2270684480 hasAuthorship W2270684480A5064797131 @default.
• W2270684480 hasAuthorship W2270684480A5068068080 @default.
• W2270684480 hasBestOaLocation W22706844801 @default.
• W2270684480 hasConcept C127413603 @default.
• W2270684480 hasConcept C155647269 @default.
• W2270684480 hasConcept C160964918 @default.
• W2270684480 hasConcept C161790260 @default.
• W2270684480 hasConcept C175156509 @default.
• W2270684480 hasConcept C178790620 @default.
• W2270684480 hasConcept C185592680 @default.
• W2270684480 hasConcept C187320778 @default.
• W2270684480 hasConcept C2778074193 @default.
• W2270684480 hasConcept C2778142098 @default.
• W2270684480 hasConcept C2778544067 @default.
• W2270684480 hasConcept C2778689049 @default.
• W2270684480 hasConcept C2778894819 @default.
• W2270684480 hasConcept C2780263894 @default.
• W2270684480 hasConcept C2780378348 @default.
• W2270684480 hasConcept C2781076698 @default.
• W2270684480 hasConcept C3044715 @default.
• W2270684480 hasConcept C43369102 @default.
• W2270684480 hasConcept C537181965 @default.
• W2270684480 hasConcept C71240020 @default.
• W2270684480 hasConceptScore W2270684480C127413603 @default.
• W2270684480 hasConceptScore W2270684480C155647269 @default.
• W2270684480 hasConceptScore W2270684480C160964918 @default.
• W2270684480 hasConceptScore W2270684480C161790260 @default.
• W2270684480 hasConceptScore W2270684480C175156509 @default.
• W2270684480 hasConceptScore W2270684480C178790620 @default.

• next