American Chemical Society
Browse

Remote Stereocontrol in the Ireland–Claisen Rearrangement by δ‑Alkoxy Group

Download (4.14 MB)
journal contribution
posted on 2023-05-09, 20:05 authored by Hye Joon Lee, Joshua J. Gladfelder, Armen Zakarian
Remote stereocontrol in the Ireland–Claisen rearrangement using a chiral acetonide that serves as internal stereocontrol element is an effective and general method for chirality transfer from a δ-hydroxyl group in the allylic alcohol unit. This strategy circumvents the need for redundant chirality at the α-position allylic alcohol, while simultaneously producing a terminal alkene that can streamline synthetic applications and complex molecule synthesis planning.

History