ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Cornforth-Evans Transition States in Stereocontrolled Allylborations of Epoxy Aldehydes.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Cornforth-Evans Transition States in Stereocontrolled Allylborations of Epoxy Aldehydes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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6 authors.
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Abstract
Allylboration reactions rank among the most reliable tools in organic synthesis. Herein, we report a general synthesis of trifunctionalized allylboronates and systematic investigations of their stereocontrolled transformations with substituted aldehyde substrates, in order to efficiently access diverse, highly substituted target substrates. A peculiar transition in stereocontrol was observed from the polar Felkin-Anh (PFA) to the Cornforth-Evans (CE) model for alkoxy- and epoxy-substituted aldehydes. CE-type transition states were uniformly identified as minima in advanced, DFT-based computational studies of allylboration reactions of epoxy aldehydes, conforming well to the experimental data, and highlighting the underestimated relevance of this model. Furthermore, a mechanism-based rationale for the substitution pattern of the epoxide was delineated that ensures high levels of stereocontrol and renders α,β-epoxy aldehydes generally applicable substrates for target synthesis.
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