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- W2014067016 abstract "We have screened a range of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts incorporating N-pyridyl and N-quinolinyl groups in the synthetically useful aldol reaction of isatin with acetone. The ‘reverse amide’ N-pyridyl pyrrolidinylmethyl amide catalysts proved highly catalytically active but gave disappointing enantioselectivities. However, an N-3-pyridyl prolinamide catalyst gave the aldol adduct in high yields and high enantioselectivity with up to 72% ee of the (S)-isomer. Conditions were optimised for this catalyst and in particular an additive screen identified a link between the pKa of the acid additive and the yield and enantioselectivity. An N-arylsulfonamide prolinamide was also identified as a catalyst for this reaction giving the (R)-enantiomer in 68% ee." @default.
- W2014067016 created "2016-06-24" @default.
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- W2014067016 creator A5073682469 @default.
- W2014067016 date "2011-07-01" @default.
- W2014067016 modified "2023-10-08" @default.
- W2014067016 title "Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin" @default.
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- W2014067016 doi "https://doi.org/10.1016/j.tetasy.2011.07.016" @default.
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