Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin

Kinsella, M. and Duggan, P.G. and Lennon, C.M. (2011) Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin. Tetrahedron Asymmetry, 22 (13). pp. 1423-1433. ISSN 0957-4166

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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.

Item Type: Article
Additional Information: Funding Information: We would like to thank the Irish Research Council for Science, Engineering and Technology and Waterford Institute of Technology for funding provided.
Uncontrolled Keywords: /dk/atira/pure/subjectarea/asjc/1500/1503
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Depositing User: Admin SSL
Date Deposited: 19 Oct 2022 23:07
Last Modified: 20 Jul 2023 19:15
URI: http://repository-testing.wit.ie/id/eprint/4152

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