FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2076609239> ?p ?o ?g. }

• W2076609239 endingPage "6808" @default.
• W2076609239 startingPage "6801" @default.
• W2076609239 abstract "Full details of the first catalytic enantioselective Reissert-type reaction are described. Utilizing the Lewis acid-Lewis base bifunctional catalyst 5 or 6 (9 mol %), the Reissert products were obtained in 57 to 99% yield with 54 to 96% ee. Electron-rich quinolines produced better yields and enantioselectivities than electron-deficient substrates. Kinetic studies indicated that the reaction should proceed via the rate-determining acyl quinolinium formation, followed by the attack of a cyanide. The catalyst does not facilitate the first rate-determining step; however, it strongly facilitates the second cyanation step. The reaction was successfully applied to an efficient catalytic asymmetric synthesis of a potent NMDA receptor antagonist (-)-L-689,560. A key step is the one-pot process using the Reissert-type reaction from quinoline 1f, followed by stereoselective reduction of the resulting enamine 2f. This step gave the key intermediate 20 in 91% yield with 93% ee, using 1 mol % of 6. The enantiomerically pure target compound was obtained through 10 operations (including recrystallization) in total yield of 47%. Furthermore, 6 was immobilized to JandaJEL, and the resulting solid-supported catalyst 11 afforded 20 in a comparable yield to the homogeneous 6, but with slightly lower enantioselectivity." @default.
• W2076609239 created "2016-06-24" @default.
• W2076609239 creator A5012101296 @default.
• W2076609239 creator A5039506911 @default.
• W2076609239 creator A5088288669 @default.
• W2076609239 creator A5090977084 @default.
• W2076609239 date "2001-06-19" @default.
• W2076609239 modified "2023-10-09" @default.
• W2076609239 title "Catalytic Enantioselective Reissert-Type Reaction: Development and Application to the Synthesis of a Potent NMDA Receptor Antagonist (−)-L-689,560 Using a Solid-Supported Catalyst" @default.
• W2076609239 cites W1963895697 @default.
• W2076609239 cites W1978171643 @default.
• W2076609239 cites W1981713650 @default.
• W2076609239 cites W1998347571 @default.
• W2076609239 cites W1998546256 @default.
• W2076609239 cites W2011007573 @default.
• W2076609239 cites W2076831847 @default.
• W2076609239 cites W2077679375 @default.
• W2076609239 cites W2083637127 @default.
• W2076609239 cites W2089420913 @default.
• W2076609239 cites W2413422602 @default.
• W2076609239 cites W2949542982 @default.
• W2076609239 cites W2949681688 @default.
• W2076609239 cites W2950436686 @default.
• W2076609239 cites W2952606897 @default.
• W2076609239 doi "https://doi.org/10.1021/ja010654n" @default.
• W2076609239 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11448184" @default.
• W2076609239 hasPublicationYear "2001" @default.
• W2076609239 type Work @default.
• W2076609239 sameAs 2076609239 @default.
• W2076609239 citedByCount "166" @default.
• W2076609239 countsByYear W20766092392012 @default.
• W2076609239 countsByYear W20766092392013 @default.
• W2076609239 countsByYear W20766092392014 @default.
• W2076609239 countsByYear W20766092392015 @default.
• W2076609239 countsByYear W20766092392016 @default.
• W2076609239 countsByYear W20766092392017 @default.
• W2076609239 countsByYear W20766092392018 @default.
• W2076609239 countsByYear W20766092392019 @default.
• W2076609239 countsByYear W20766092392020 @default.
• W2076609239 countsByYear W20766092392021 @default.
• W2076609239 countsByYear W20766092392022 @default.
• W2076609239 countsByYear W20766092392023 @default.
• W2076609239 crossrefType "journal-article" @default.
• W2076609239 hasAuthorship W2076609239A5012101296 @default.
• W2076609239 hasAuthorship W2076609239A5039506911 @default.
• W2076609239 hasAuthorship W2076609239A5088288669 @default.
• W2076609239 hasAuthorship W2076609239A5090977084 @default.
• W2076609239 hasConcept C134121241 @default.
• W2076609239 hasConcept C146686406 @default.
• W2076609239 hasConcept C155647269 @default.
• W2076609239 hasConcept C161790260 @default.
• W2076609239 hasConcept C163638829 @default.
• W2076609239 hasConcept C178790620 @default.
• W2076609239 hasConcept C185592680 @default.
• W2076609239 hasConcept C191897082 @default.
• W2076609239 hasConcept C192562407 @default.
• W2076609239 hasConcept C21951064 @default.
• W2076609239 hasConcept C2776378156 @default.
• W2076609239 hasConcept C2779380150 @default.
• W2076609239 hasConcept C2779412933 @default.
• W2076609239 hasConcept C2780443040 @default.
• W2076609239 hasConcept C28173026 @default.
• W2076609239 hasConcept C71240020 @default.
• W2076609239 hasConceptScore W2076609239C134121241 @default.
• W2076609239 hasConceptScore W2076609239C146686406 @default.
• W2076609239 hasConceptScore W2076609239C155647269 @default.
• W2076609239 hasConceptScore W2076609239C161790260 @default.
• W2076609239 hasConceptScore W2076609239C163638829 @default.
• W2076609239 hasConceptScore W2076609239C178790620 @default.
• W2076609239 hasConceptScore W2076609239C185592680 @default.
• W2076609239 hasConceptScore W2076609239C191897082 @default.
• W2076609239 hasConceptScore W2076609239C192562407 @default.
• W2076609239 hasConceptScore W2076609239C21951064 @default.
• W2076609239 hasConceptScore W2076609239C2776378156 @default.
• W2076609239 hasConceptScore W2076609239C2779380150 @default.
• W2076609239 hasConceptScore W2076609239C2779412933 @default.
• W2076609239 hasConceptScore W2076609239C2780443040 @default.
• W2076609239 hasConceptScore W2076609239C28173026 @default.
• W2076609239 hasConceptScore W2076609239C71240020 @default.
• W2076609239 hasIssue "28" @default.
• W2076609239 hasLocation W20766092391 @default.
• W2076609239 hasLocation W20766092392 @default.
• W2076609239 hasOpenAccess W2076609239 @default.
• W2076609239 hasPrimaryLocation W20766092391 @default.
• W2076609239 hasRelatedWork W1979861207 @default.
• W2076609239 hasRelatedWork W1989820648 @default.
• W2076609239 hasRelatedWork W2084833818 @default.
• W2076609239 hasRelatedWork W2095264474 @default.
• W2076609239 hasRelatedWork W2134265167 @default.
• W2076609239 hasRelatedWork W2150200840 @default.
• W2076609239 hasRelatedWork W2915648472 @default.
• W2076609239 hasRelatedWork W2949405405 @default.
• W2076609239 hasRelatedWork W3156437978 @default.
• W2076609239 hasRelatedWork W4313400078 @default.
• W2076609239 hasVolume "123" @default.
• W2076609239 isParatext "false" @default.
• W2076609239 isRetracted "false" @default.
• W2076609239 magId "2076609239" @default.

• next