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F10BINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes

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Abstract

An F10BINOL-derived chiral phosphoric acid was shown to be an effective catalyst for an enantioselective carbonyl-ene reaction of 1,1-disubstituted olefins with ethyl glyoxylate as the common enophile. The perfluoro-binaphthyl skeleton is beneficial not only for adopting high catalytic activity but also for creating an effective chiral environment for enantioselective transformations. Indeed, the reaction afforded enantio-enriched homoallylic alcohols in high yields with high enantioselectivities. Theoretical studies identified that the multi-point C–H⋯O hydrogen bonds and the π interactions between the substrates and the 6-methoxy-2-naphthyl substituents at the 3,3′-positions of the F10BINOL skeleton play a crucial role in determining the stereochemical outcomes. The significance of the perfluoro-binaphthyl skeleton in achieving the high enantioselectivity was also evaluated through a structural analysis of the catalysts.

Graphical abstract: F10BINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes

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Publication details

The article was received on 13 Aug 2018, accepted on 17 Nov 2018 and first published on 19 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC03587C
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    F10BINOL-derived chiral phosphoric acid-catalyzed enantioselective carbonyl-ene reaction: theoretical elucidation of stereochemical outcomes

    J. Kikuchi, H. Aramaki, H. Okamoto and M. Terada, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC03587C

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