Matches in SemOpenAlex for { <https://semopenalex.org/work/W2076535575> ?p ?o ?g. }
- W2076535575 endingPage "115" @default.
- W2076535575 startingPage "104" @default.
- W2076535575 abstract "The enantioselective hydrogenation of 2,2,2-trifluoroacetophenone (1) on cinchona-modified Pt, combined with the diastereoselective hydrogenation of cinchonidine and NMR analysis of the modifier–substrate–product interactions, revealed the key role of the product (S)-1-phenyl-2,2,2-trifluoroethanol (2) in enantioselection. We propose a multiple cycle mechanism including a racemic route (a) on the unmodified sites and three enantioselective routes. In the enantioselective cycles, there is an N–H–O type interaction between the quinuclidine N and the carbonyl O-atom of the substrate. At low conversion, the alkaloid alone is the source of chiral information (route b). With increasing conversion, the weakly acidic minor product (S)-2 forms an adduct with the alkaloid and this complex controls the enantioselection (route c, lower ee). The frequently applied strong acid additive TFA replaces (S)-2 and the alkaloid–TFA complex gives the highest ee (route d). The diastereoselective hydrogenation of cinchonidine disproves a former mechanistic model proposed in the literature." @default.
- W2076535575 created "2016-06-24" @default.
- W2076535575 creator A5023557325 @default.
- W2076535575 creator A5037313133 @default.
- W2076535575 creator A5040833016 @default.
- W2076535575 creator A5042463535 @default.
- W2076535575 creator A5052634322 @default.
- W2076535575 creator A5034182285 @default.
- W2076535575 date "2011-05-01" @default.
- W2076535575 modified "2023-10-05" @default.
- W2076535575 title "Multiple cycle reaction mechanism in the enantioselective hydrogenation of α,α,α-trifluoromethyl ketones" @default.
- W2076535575 cites W104489237 @default.
- W2076535575 cites W106427786 @default.
- W2076535575 cites W147608629 @default.
- W2076535575 cites W191817941 @default.
- W2076535575 cites W1965304483 @default.
- W2076535575 cites W1966095929 @default.
- W2076535575 cites W1969462406 @default.
- W2076535575 cites W1971169623 @default.
- W2076535575 cites W1974311061 @default.
- W2076535575 cites W1976085475 @default.
- W2076535575 cites W1977986278 @default.
- W2076535575 cites W1978743038 @default.
- W2076535575 cites W1981753990 @default.
- W2076535575 cites W1983710190 @default.
- W2076535575 cites W1986129072 @default.
- W2076535575 cites W1987206449 @default.
- W2076535575 cites W1991836332 @default.
- W2076535575 cites W1995036792 @default.
- W2076535575 cites W1998746189 @default.
- W2076535575 cites W1999381351 @default.
- W2076535575 cites W2000105907 @default.
- W2076535575 cites W2005885040 @default.
- W2076535575 cites W2006577807 @default.
- W2076535575 cites W2006805069 @default.
- W2076535575 cites W2018399161 @default.
- W2076535575 cites W2020855738 @default.
- W2076535575 cites W2022673999 @default.
- W2076535575 cites W2023497601 @default.
- W2076535575 cites W2023688191 @default.
- W2076535575 cites W2027325228 @default.
- W2076535575 cites W2036121960 @default.
- W2076535575 cites W2045840381 @default.
- W2076535575 cites W2052186324 @default.
- W2076535575 cites W2054140636 @default.
- W2076535575 cites W2057225329 @default.
- W2076535575 cites W2059344169 @default.
- W2076535575 cites W2062787826 @default.
- W2076535575 cites W2063185182 @default.
- W2076535575 cites W2067642651 @default.
- W2076535575 cites W2069928356 @default.
- W2076535575 cites W2070700870 @default.
- W2076535575 cites W2075972728 @default.
- W2076535575 cites W2076313269 @default.
- W2076535575 cites W2076639288 @default.
- W2076535575 cites W2081080412 @default.
- W2076535575 cites W2083036395 @default.
- W2076535575 cites W2083038057 @default.
- W2076535575 cites W2084761689 @default.
- W2076535575 cites W2086040247 @default.
- W2076535575 cites W2092555050 @default.
- W2076535575 cites W2094917763 @default.
- W2076535575 cites W2097001897 @default.
- W2076535575 cites W2120634307 @default.
- W2076535575 cites W2130936748 @default.
- W2076535575 cites W2154588237 @default.
- W2076535575 cites W2169530885 @default.
- W2076535575 cites W2517314999 @default.
- W2076535575 cites W2952354393 @default.
- W2076535575 cites W4233816293 @default.
- W2076535575 doi "https://doi.org/10.1016/j.jcat.2011.03.009" @default.
- W2076535575 hasPublicationYear "2011" @default.
- W2076535575 type Work @default.
- W2076535575 sameAs 2076535575 @default.
- W2076535575 citedByCount "25" @default.
- W2076535575 countsByYear W20765355752012 @default.
- W2076535575 countsByYear W20765355752013 @default.
- W2076535575 countsByYear W20765355752014 @default.
- W2076535575 countsByYear W20765355752015 @default.
- W2076535575 countsByYear W20765355752017 @default.
- W2076535575 countsByYear W20765355752018 @default.
- W2076535575 countsByYear W20765355752020 @default.
- W2076535575 countsByYear W20765355752022 @default.
- W2076535575 crossrefType "journal-article" @default.
- W2076535575 hasAuthorship W2076535575A5023557325 @default.
- W2076535575 hasAuthorship W2076535575A5034182285 @default.
- W2076535575 hasAuthorship W2076535575A5037313133 @default.
- W2076535575 hasAuthorship W2076535575A5040833016 @default.
- W2076535575 hasAuthorship W2076535575A5042463535 @default.
- W2076535575 hasAuthorship W2076535575A5052634322 @default.
- W2076535575 hasConcept C111368507 @default.
- W2076535575 hasConcept C127313418 @default.
- W2076535575 hasConcept C146686406 @default.
- W2076535575 hasConcept C155647269 @default.
- W2076535575 hasConcept C161790260 @default.
- W2076535575 hasConcept C178790620 @default.
- W2076535575 hasConcept C185592680 @default.
- W2076535575 hasConcept C2776442012 @default.