posted on 2023-05-09, 20:05authored byHye 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.