Diastereoselective sulfur ylide rearrangements from gold catalysed oxidation of ynamides
Research output: Contribution to journal › Article › peer-review
Colleges, School and Institutes
The [2,3]-sigmatropic rearrangement of sulfonium ylides bearing substituted allyl groups creates two contiguous stereocentres. Low diastereoselectivity is typically observed from commonly used α-diazocarboxylic ester precursors. High diastereoselectivity was previously revealed in a gold-catalyzed multicomponent route into allyl sulfonium ylides by reaction of ynamide, oxidant and allyl sulfides. The effect of substrate modifications on the diastereoselectivity have been studied, with N-phenyl methanesulfonamide derived ynamides proving the most effective. This report includes an enhanced experimental procedure, and a demonstration that the gold-catalyzed process remains highly effective at −78 °C.
|Early online date||13 Nov 2020|
|Publication status||Published - 8 Jan 2021|
- Sulfur ylide, Rearrangement, Gold carbenoid, Oxidation, Ynamide