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New observations in organozinc chemistry: Control of relative stereochemistry in reactions of silicon substituted alkenylzinc reagents
journal contributionposted on 2023-06-07, 19:07 authored by Eddy Viseux, P J Parsons, J B J Pavey
Reagents have been synthesised that behave as both Lewis acids and nucleophiles. Reaction of these reagents with electrophiles has led to the finding that diastereoselectivity is observed upon addition to aldehydes. An ordered transition state to account for the observed stereochemistry is proposed herein
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NotesEMEV did all the synthetic work and co wrote the paper. This paper features the use of binucleophilic reagents to access homoallylic alcohols with apparent silicon shift and good to excellent diastereocontrol. This methodology is of particular interest to assemble complex molecules in a rapid and efficient manner.
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