American Chemical Society
jo3c00535_si_002.pdf (4.14 MB)

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

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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.