Enantioselective Synthesis of Skipped Dienes via Iridium-Catalyzed Allylic Alkylation of Phosphonate Carbanions

01 September 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


An enantioselective synthesis of skipped diene has been developed based on an iridium-catalyzed allylic alkylation of phosphonate carbanions and Horner-Wadsworth-Emmons olefination. This two-step protocol benefits from the ease of accessibility of the starting materials and delivers C2-substituted skipped dienes, bearing a C3 stereogenic center, in moderate to excellent yields and generally with outstanding enantioselectivities. This is the first catalytic enantioselective allylic alkylation of phosphonate carbanions.


allylic alkylation
skipped diene
iridium catalysis
phosphonate carbanion
allylic substitution


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