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Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid

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Abstract

Enantioselective intramolecular [3 + 2] annulation of chalcones bearing an allene moiety has been successfully developed. The reaction was effectively promoted by amino acid-derived phosphines, in combination with achiral Brønsted acids. Dihydrocoumarin architectures were constructed in high yields and with excellent enantiomeric excesses. Theoretical studies via DFT calculations revealed that the hydrogen bonding network induced by achiral Brønsted acids/chiral phosphines could more efficiently distinguish between two enantioselective pathways, thus leading to enhanced enantioselectivity.

Graphical abstract: Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid

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Publication details

The article was received on 01 Mar 2017, accepted on 13 May 2017 and first published on 17 May 2017


Article type: Edge Article
DOI: 10.1039/C7SC00952F
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid

    W. Yao, Z. Yu, S. Wen, H. Ni, N. Ullah, Y. Lan and Y. Lu, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC00952F

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