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Issue 8, 2017
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Asymmetric synthesis of chromans via the Friedel–Crafts alkylation–hemiketalization catalysed by an N,N′-dioxide scandium(III) complex

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Abstract

An enantioselective tandem Friedel–Crafts alkylation–hemiketalization between electron-rich phenols and α,β-unsaturated ketoesters gave a direct approach to chiral 2,3-disubstituted chromans in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex. High enantioselectivities (up to 95% ee), high diastereoselectivities (up to 14 : 1) and high yields (up to 97%) were obtained for a broad range of substrates under mild reaction conditions.

Graphical abstract: Asymmetric synthesis of chromans via the Friedel–Crafts alkylation–hemiketalization catalysed by an N,N′-dioxide scandium(iii) complex

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Publication details

The article was received on 25 Apr 2017, accepted on 18 May 2017 and first published on 19 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00323D
Citation: Org. Chem. Front., 2017,4, 1647-1650
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    Asymmetric synthesis of chromans via the Friedel–Crafts alkylation–hemiketalization catalysed by an N,N′-dioxide scandium(III) complex

    X. Hao, L. Lin, F. Tan, S. Ge, X. Liu and X. Feng, Org. Chem. Front., 2017, 4, 1647
    DOI: 10.1039/C7QO00323D

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