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Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters

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Abstract

The isothiourea-catalysed enantioselective Michael addition of 3-aryloxindole and 4-substituted-dihydropyrazol-3-one pronucleophiles to α,β-unsaturated p-nitrophenyl esters is reported. This process generates products containing two contiguous stereocentres, one quaternary, in good yields and excellent enantioselectivities (>30 examples, up to > 95 : 5 dr and 99 : 1 er). This protocol harnesses the multifunctional ability of p-nitrophenoxide to promote effective catalysis. In contrast to previous methodologies using tertiary amine Lewis bases, in which the pronucleophile was used as the solvent, this work allows bespoke pronucleophiles to be used in stoichiometric quantities.

Graphical abstract: Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters

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Publication details

The article was received on 26 Aug 2019, accepted on 13 Oct 2019 and first published on 23 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC04303A
Chem. Sci., 2020, Advance Article
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    Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters

    C. Shu, H. Liu, A. M. Z. Slawin, C. Carpenter-Warren and A. D. Smith, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04303A

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