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

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 m...

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Bibliographic Details
Published inJournal of chemical education Vol. 89; no. 6; pp. 799 - 802
Main Authors Candeias, Nuno R, Paterna, Roberta, Cal, Pedro M. S. D, Góis, Pedro M. P
Format Journal Article
LanguageEnglish
Published Easton American Chemical Society and Division of Chemical Education, Inc 08.05.2012
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society
American Chemical Society
Subjects
Chemical reactions
Curricula
Experiments
Organic Chemistry
Protocol
Reagents
Science education
Hands-On Learning/Manipulatives
Amines/Ammonium Compounds
NMR Spectroscopy
Upper-Division Undergraduate
Synthesis
Laboratory Instruction
Diastereomers
Water/Water Chemistry
Organic Chemistry
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Summary: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed200509q