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Secondary stereocontrolling interactions in chiral Brønsted acid catalysis: study of a Petasis–Ferrier-type rearrangement catalyzed by chiral phosphoric acids

Chemical science (Cambridge), 2014, Vol.5 (9), p.3515-3523 [Peer Reviewed Journal]

ISSN: 2041-6520 ;EISSN: 2041-6539 ;DOI: 10.1039/C4SC00611A

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  • Title:
    Secondary stereocontrolling interactions in chiral Brønsted acid catalysis: study of a Petasis–Ferrier-type rearrangement catalyzed by chiral phosphoric acids
  • Author: Kanomata, Kyohei ; Toda, Yasunori ; Shibata, Yukihiro ; Yamanaka, Masahiro ; Tsuzuki, Seiji ; Gridnev, Ilya D. ; Terada, Masahiro
  • Is Part Of: Chemical science (Cambridge), 2014, Vol.5 (9), p.3515-3523
  • Description: Chiral phosphoric acids have emerged as promising asymmetric Brønsted acid catalysts that harness hydrogen bonding interactions as key stereocontrolling elements. A new approach to chiral phosphoric acid catalysis through ion-pairing interactions between the anionic conjugate base of the catalyst and a cationic electrophile has recently attracted attention. However, the mechanism of stereocontrol through ion-pairing interactions is still elusive. As a probe reaction for studying the stereocontrolling element involved in such catalytic reactions, we investigated the Petasis–Ferrier-type rearrangement of a 7-membered cyclic vinyl acetal catalyzed by chiral phosphoric acids. DFT calculations suggested that non-classical C–H⋯O hydrogen bonds between the catalyst and the substrate play an important role in determining the stereoselectivity. In addition, π–π stacking interactions were found to be a key factor for stereocontrol when using a 9-anthryl group-bearing catalyst.
  • Language: English
  • Identifier: ISSN: 2041-6520
    EISSN: 2041-6539
    DOI: 10.1039/C4SC00611A
  • Source: Open Access: PubMed Central
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