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Issue 3, 2016
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Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters

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Abstract

Catalytic, enantioselective [3 + 2] cycloadditions of azomethine ylides derived from alanine imino esters with 3-nitroindoles are reported. The dearomative cycloaddition reactions occur in the presence of a catalyst generated in situ from Cu(OTf)2 and (R)-Difluorphos to form exo′-pyrroloindoline cycloadducts and establish four contiguous stereogenic centers, two of which are fully substituted. The exo′-pyrroloindoline products are formed in moderate-to-good yields (39–85%) with high diastereoselectivities (up to 98 : 1 : 1 dr) and enantioselectivities (up to 96% ee).

Graphical abstract: Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters

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Publication details

The article was received on 03 Nov 2015, accepted on 27 Dec 2015 and first published on 04 Jan 2016


Article type: Research Article
DOI: 10.1039/C5QO00346F
Citation: Org. Chem. Front., 2016,3, 339-343
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    Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters

    A. L. Gerten and L. M. Stanley, Org. Chem. Front., 2016, 3, 339
    DOI: 10.1039/C5QO00346F

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