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

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 a...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-06, Vol.88 (11), p.7560-7563
Main Authors: Lee, Hye Joon, Gladfelder, Joshua J., Zakarian, Armen
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00535