Combined C-H Functionalization/Cope Rearrangement with Vinyl Ethers as a Surrogate for the Vinylogous Mukaiyama Aldol Reaction

Lian, Y., Davies, H. M. L.

J. Am. Chem. Soc.,
2011, 11940-11943; 10.1021/ja2051155


The CCHF is seeking not only to establish the current C–H Functionalization reactions as powerful transformations for organic synthesis, but develop new and enabling methodologies.

A great deal of work has been done recently in understanding the combined C–H Functionalization/Cope-rearrangement reaction. With this increased understanding has come guidance on ways in which the reaction can be developed and the scope extended.

This report describes how using the lessons learnt from previous studies within the CCHF the chemistry can be adapted and used to create a new transformation. It is now possible to acheive the products typically associated with the more traditional vinylogous Mukaiyama aldol reaction, in a more streamlined and sustainable fashion using C–H Functionalization.

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