A Sustainable Protocol for the Aqueous Multicomponent Petasis Borono-Mannich Reaction

Nuno R. Candeias, Roberta Paterna, Pedro M. S. D. Cal, Pedro M. P. Gois

    Research output: Contribution to journalArticleScientificpeer-review

    17 Citations (Scopus)

    Abstract

    A protocol for the preparation of Petasis borono Mannich products suitable for advanced organic chemistry experiments, using water as a reaction medium, was developed. The experiment is carried out in less than 4 h (with a 30 min pre-session on the day before) using commercially available starting materials in the preparation of phenylglycine and 2-hydroxymorpholine derivatives. These experiments are useful in the organic chemistry curriculum for the introduction of multicomponent reactions and for the use of boronic acids and water as environmentally friendly reagents and solvent, respectively.

    Original languageEnglish
    Pages (from-to)799-802
    Number of pages4
    JournalJournal of Chemical Education
    Volume89
    Issue number6
    DOIs
    Publication statusPublished - Jun 2012
    Publication typeA1 Journal article-refereed

    Funding

    We would like to acknowledge the undergraduate students from the integrated masters of pharmaceutical sciences from the Faculty of Pharmacy of University of Lisbon that conducted these experiments and Fundacao para a Ciencia e Tecnologia and FEDER (Ref. PTDC/QUI/66695/2006, Ref. SFRH/BPD/46589/2008 and Ref. SFRH/BD/72376/2010) for the financial support.

    Keywords

    • Upper-Division Undergraduate
    • Laboratory Instruction
    • Organic Chemistry
    • Hands-On Learning/Manipulatives
    • Amines/Ammonium Compounds
    • Diastereomers
    • NMR Spectroscopy
    • Synthesis
    • Water/Water Chemistry
    • DIELS-ALDER REACTIONS
    • ALPHA-AMINO-ACIDS
    • GREEN CHEMISTRY
    • ALCOHOLS
    • 2-HYDROXYMORPHOLINES
    • 2H-CHROMENES
    • ALDEHYDES
    • WATER

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