Matches in SemOpenAlex for { <https://semopenalex.org/work/W2320062088> ?p ?o ?g. }
- W2320062088 endingPage "3261" @default.
- W2320062088 startingPage "3252" @default.
- W2320062088 abstract "The diastereo- and enantioselectivity obtained experimentally by Christmann in the amine-catalyzed intramolecular Diels-Alder reaction of α,β-unsaturated carbonylic compounds were fully rationalized using density functional theory methods at the PBE1PBE/6-311+G** level. A polarizable continuum model was used to describe solvent effects. The selectivity is induced in the cyclization step, and while the enantioselectivity results from the syn/anti orientation around the C-N enamine bond, the diastereoselectivity mainly results from the syn/anti configuration of the substituents in the forming cyclopentane ring. The remarkable reaction rate experimentally observed when an external protic acid is used is attributed to the strong decrease in the activation energy of all steps needed for the enamine formation, while the external acid marginally influences the cyclization step. When hydrogen-bond-donor catalysts are used, the formation of one hydrogen bond in the cyclization step inverts the configuration and reduces the selectivity. The different behavior between dialdehydes and ketoaldehydes is suggested to be resulting from different reaction rates in the catalyst elimination step." @default.
- W2320062088 created "2016-06-24" @default.
- W2320062088 creator A5007342971 @default.
- W2320062088 creator A5071141319 @default.
- W2320062088 date "2012-03-14" @default.
- W2320062088 modified "2023-10-18" @default.
- W2320062088 title "Enantioselective Organocatalytic Intramolecular Diels–Alder Reactions: A Computational Study" @default.
- W2320062088 cites W1501145371 @default.
- W2320062088 cites W1969038965 @default.
- W2320062088 cites W1972024949 @default.
- W2320062088 cites W1981368803 @default.
- W2320062088 cites W1989368783 @default.
- W2320062088 cites W1992725819 @default.
- W2320062088 cites W1996483627 @default.
- W2320062088 cites W1997002640 @default.
- W2320062088 cites W1997151511 @default.
- W2320062088 cites W2004056887 @default.
- W2320062088 cites W2008423326 @default.
- W2320062088 cites W2010891242 @default.
- W2320062088 cites W2012961504 @default.
- W2320062088 cites W2013624967 @default.
- W2320062088 cites W2021846814 @default.
- W2320062088 cites W2023271753 @default.
- W2320062088 cites W2031068701 @default.
- W2320062088 cites W2036319937 @default.
- W2320062088 cites W2045830377 @default.
- W2320062088 cites W2047100973 @default.
- W2320062088 cites W2054704030 @default.
- W2320062088 cites W2054788360 @default.
- W2320062088 cites W2062355662 @default.
- W2320062088 cites W2066889571 @default.
- W2320062088 cites W2072964465 @default.
- W2320062088 cites W2075572227 @default.
- W2320062088 cites W2094818492 @default.
- W2320062088 cites W2112850441 @default.
- W2320062088 cites W2114379277 @default.
- W2320062088 cites W2141815448 @default.
- W2320062088 cites W2143981217 @default.
- W2320062088 cites W2147484807 @default.
- W2320062088 cites W2150697053 @default.
- W2320062088 cites W2153567404 @default.
- W2320062088 cites W2163861916 @default.
- W2320062088 cites W2165291048 @default.
- W2320062088 cites W2166796782 @default.
- W2320062088 cites W2169154681 @default.
- W2320062088 cites W2949169798 @default.
- W2320062088 cites W2950072447 @default.
- W2320062088 cites W2950142963 @default.
- W2320062088 cites W2951762364 @default.
- W2320062088 cites W2952554152 @default.
- W2320062088 cites W4237804782 @default.
- W2320062088 cites W4244156341 @default.
- W2320062088 cites W4366716063 @default.
- W2320062088 cites W4375905839 @default.
- W2320062088 doi "https://doi.org/10.1021/jo300005e" @default.
- W2320062088 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22364202" @default.
- W2320062088 hasPublicationYear "2012" @default.
- W2320062088 type Work @default.
- W2320062088 sameAs 2320062088 @default.
- W2320062088 citedByCount "18" @default.
- W2320062088 countsByYear W23200620882012 @default.
- W2320062088 countsByYear W23200620882013 @default.
- W2320062088 countsByYear W23200620882014 @default.
- W2320062088 countsByYear W23200620882015 @default.
- W2320062088 countsByYear W23200620882016 @default.
- W2320062088 countsByYear W23200620882018 @default.
- W2320062088 countsByYear W23200620882020 @default.
- W2320062088 countsByYear W23200620882022 @default.
- W2320062088 crossrefType "journal-article" @default.
- W2320062088 hasAuthorship W2320062088A5007342971 @default.
- W2320062088 hasAuthorship W2320062088A5071141319 @default.
- W2320062088 hasConcept C112887158 @default.
- W2320062088 hasConcept C118792377 @default.
- W2320062088 hasConcept C132439834 @default.
- W2320062088 hasConcept C146686406 @default.
- W2320062088 hasConcept C147597530 @default.
- W2320062088 hasConcept C152365726 @default.
- W2320062088 hasConcept C155647269 @default.
- W2320062088 hasConcept C161790260 @default.
- W2320062088 hasConcept C176933379 @default.
- W2320062088 hasConcept C178790620 @default.
- W2320062088 hasConcept C185592680 @default.
- W2320062088 hasConcept C2776122248 @default.
- W2320062088 hasConcept C2776378156 @default.
- W2320062088 hasConcept C2778556512 @default.
- W2320062088 hasConcept C2778733088 @default.
- W2320062088 hasConcept C2779940776 @default.
- W2320062088 hasConcept C2780471494 @default.
- W2320062088 hasConcept C32909587 @default.
- W2320062088 hasConcept C71240020 @default.
- W2320062088 hasConcept C75079739 @default.
- W2320062088 hasConceptScore W2320062088C112887158 @default.
- W2320062088 hasConceptScore W2320062088C118792377 @default.
- W2320062088 hasConceptScore W2320062088C132439834 @default.
- W2320062088 hasConceptScore W2320062088C146686406 @default.
- W2320062088 hasConceptScore W2320062088C147597530 @default.
- W2320062088 hasConceptScore W2320062088C152365726 @default.
- W2320062088 hasConceptScore W2320062088C155647269 @default.