The Boronic Mannich Reaction in a Solid-Phase Approach

We report herein the use of the multi-component boronic Mannich reaction (BMR) in a solid-phase approach, in which an aryl boronic acid is combined with an aldehyde and a secondary amine. We describe several examples, in which each of the three components is alternately anchored onto Wang polystyren...

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Bibliographic Details
Published in:Tetrahedron 2000-12, Vol.56 (51), p.10023-10030
Main Authors: Schlienger, Nathalie, Bryce, Martin R., Hansen, Thomas K.
Format: Article
Language:English
Subjects:
amino acids and derivatives
boron and compounds
Mannich reactions
solid-phase synthesis
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Summary:We report herein the use of the multi-component boronic Mannich reaction (BMR) in a solid-phase approach, in which an aryl boronic acid is combined with an aldehyde and a secondary amine. We describe several examples, in which each of the three components is alternately anchored onto Wang polystyrene, giving in most cases (but not all) the expected products in high yields and purities. We also suggest, based on 11B NMR studies, that the intermediate formation of a tetracoordinated boron species could represent the prerequisite for success of the BMR.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00957-1