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DOI: 10.1055/s-0040-1719708
Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reactions
Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reactions.
Science 2021;
371: 380-386
DOI: 10.1126/science.abd6095.
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Significance
The You group reports two unique methods for enantioselective iridium-catalyzed allylic substitution reactions, which are highly selective for the thermodynamically less stable Z-alkene products. Conventionally, metal-catalyzed asymmetric allylic substitution reactions favor the E-isomer of the products.
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Comment
The authors rationalized their reaction design by focusing on developing a catalytic system that allowed for a slow isomerization from the initial anti-π-allyl complex to the more favored syn-π-allyl species. Subsequent capture of the chiral anti-π-iridium species by a nucleophile selectively generated the enantioenriched Z-alkene products.
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Publication History
Article published online:
20 April 2021
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