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Issue 40, 2017
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An enantioselective synthesis of spiro-oxindole-based 3,4-dihydropyrroles via a Michael/cyclization cascade of 3-aminooxindoles with 2-enoylpyridines

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Abstract

An organocatalytic and highly diastereo- and enantioselective reaction of 3-aminooxindoles with 2-enoylpyridines for the synthesis of chiral spiro[pyrrolidin-3,2′-oxindole] derivatives has been achieved. With the cinchonidine-based thiourea catalyst, the asymmetric Michael/cyclization reaction sequence of 3-aminooxindoles with 2-enoylpyridines followed by the dehydration and deprotection with concentrated hydrochloric acid provided a wide range of chiral 3′,4′-dihydrospiro[indoline-3,2′-pyrrol]-2-ones, bearing two adjacent tri- and tetrasubstituted stereocenters, in moderate to good yields with overall excellent stereoselectivities. The synthetic application of this methodology was presented by the scale-up experiment and transformation of product 5a into the spiro-oxindole-based pyrrolidine 6. Furthermore, a plausible transition state for this cascade reaction sequence was also proposed. And this work will provide a new way to access chiral spiro[pyrrolidin-3,2′-oxindole] derivatives.

Graphical abstract: An enantioselective synthesis of spiro-oxindole-based 3,4-dihydropyrroles via a Michael/cyclization cascade of 3-aminooxindoles with 2-enoylpyridines

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Publication details

The article was received on 27 Aug 2017, accepted on 21 Sep 2017 and first published on 21 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02138K
Citation: Org. Biomol. Chem., 2017,15, 8518-8522
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    An enantioselective synthesis of spiro-oxindole-based 3,4-dihydropyrroles via a Michael/cyclization cascade of 3-aminooxindoles with 2-enoylpyridines

    B. Cui, Y. Chen, J. Shan, L. Qin, C. Yuan, Y. Wang, W. Han, N. Wan and Y. Chen, Org. Biomol. Chem., 2017, 15, 8518
    DOI: 10.1039/C7OB02138K

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