Secondary-Sphere Modification in Proline Catalysis: Old Friend, New Connection

Ido Domb, Danilo M. Lustosa, Anat Milo

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

In this work, we exploit our strategy of in situ secondary-sphere modification of organocatalysts to improve the reactivity and selectivity of amino catalysts. Herein, the carboxylic acid moiety of proline was targeted as a site for modification under catalytic reaction conditions with boronic acids. Intermolecular aldol reactions between aromatic aldehydes and cyclopentanone were selected as a proof-of-concept because cyclopentanone as an aldol donor was often associated with decreased selectivity compared to its 6-membered ring analog, hexanone. Our secondary-sphere modification strategy, using naturally occurring l-proline amino acid, enabled reactions at room temperature with high levels of diastereo- and enantio-selectivity and short reaction times. NMR and HR-MS studies shed light on the nature of the catalyst structure and on the role of water in our reactions. This journal is

Original languageEnglish
Pages (from-to)1950-1953
Number of pages4
JournalChemical Communications
Volume58
Issue number12
Early online date19 Jan 2022
DOIs
StatePublished - 11 Feb 2022

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry (all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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