An enantioselective synthesis of skipped dienes has been
developed
based on an iridium-catalyzed allylic alkylation of phosphonates and
Horner–Wadsworth–Emmons olefination. This two-step protocol
uses easily accessible substrates and delivers C2-substituted skipped
dienes bearing a C3 stereogenic center, generally with outstanding
enantioselectivities (up to 99.5:0.5 er). This is the first catalytic
enantioselective allylic alkylation of phosphonates, and the overall
process represents a formal enantioselective α-C(sp2)–H allylic alkylation of α,β-unsaturated carbonyls
and acrylonitrile.
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.
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