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Published May 26, 2023 | Published + Supplemental Material
Journal Article Open

α-Vinylation of Ester Equivalents via Main Group Catalysis for the Construction of Quaternary Centers

Abstract

A methodology for the construction of sterically congested quaternary centers via the trapping of vinyl carbocations with silyl ketene acetals is disclosed. This main group-catalyzed α-vinylation reaction is advantageous as methods to access these congested motifs are limited. Moreover, β,γ-unsaturated carbonyl moieties and tetrasubstituted alkenes are present in various bioactive natural products and pharmaceuticals, and this catalytic platform offers a means of accessing them using simple and inexpensive materials.

Additional Information

© 2023 The Authors. Published by American Chemical Society. Attribution 4.0 International (CC BY 4.0) Financial support for this work was provided by the Alfred P. Sloan Foundation (to H.M.N.) and the National Institute of Health National Institute of General Medical Sciences (R35 GM128936 to H.M.N.). The authors thank the Beckman Institute (support of the Caltech Center for Catalysis and Chemical Synthesis). The authors thank Dr. Scott Virgil for instrumentation and Dr. Mona Shahgholi for mass spectrometry support. The authors declare no competing financial interest.

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Published - acs.orglett.3c00535.pdf

Supplemental Material - ol3c00535_si_001.pdf

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Additional details

Created:
August 22, 2023
Modified:
October 20, 2023