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Updated: Jun 27, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Stereopentads derived from a sequence of Mukaiyama aldolization and free radical reduction on
Jean-François Brazeau1, Philippe Mochirian, Michel Prévost
1Institut de recherches cliniques de Montréal, Bio-organic Chemistry Laboratory, 110 Avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7.
Abstract:
In a stereodivergent manner, all 16 diastereomeric stereopentads 7-22 were synthesized starting with alpha-methyl-beta-alkoxy aldehydes 25 and 27. We designed an approach based on a sequence of a Mukaiyama aldolization with enoxysilane 24 followed by a hydrogen transfer reaction. Recent advancements concerning these reactions are described, and novel key intermediates are characterized in the aldol step. The synthesis of C(1)-C(11) fragment 60 of zincophorin, which contains a synthetically challenging stereopentad unit, is described attesting the usefulness of our strategy.
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