The Ireland-Claisen [3,3]-sigmatropic rearrangement of an allylic glycinate bearing a remote chiral enol ether has been studied. Remote exopericyclic stereocontrol is achievable in this instance. The product from this rearrangement has been progressed through a formal total synthesis of the natural antibiotic, furanomycin.
- amino acid
Tellam, J. P., & Carbery, D. R. (2011). Ireland-Claisen rearrangement of substrates bearing chiral enol ether units. Tetrahedron Letters, 52(45), 6027-6029. https://doi.org/10.1016/j.tetlet.2011.09.011