Difluoroenoxysilanes\nin Catalytic Asymmetric Allylic\nAlkylation

An allylic substitution with difluoroenoxysilanes as\nthe nucleophile\nis accomplished for the enantioselective synthesis of α-allylic\nα,α-difluoroketones. With racemic branched allylic alcohols\nas the easily accessible allylic electrophile, this branched-selective\nand enantioconvergent allylic alkylation reaction is catalyzed by\nan Ir(I)/(<i>P</i>,olefin) complex and overcomes the low\nnucleophilicity of difluoroenoxysilanes to furnish β-chiral\nα,α-difluoroketones in moderate to good yields with high\nenantioselectivity (up to >99.9:0.1 er).

Publication Details

Journal
Figshare
Published
2024-12-04
DOI
https://doi.org/10.1021/acs.orglett.4c04279.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
Field-Weighted Citation Impact
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article

Difluoroenoxysilanes\nin Catalytic Asymmetric Allylic\nAlkylation

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Mycorrhizal Fungi and Plant Interactions
article

Difluoroenoxysilanes\nin Catalytic Asymmetric Allylic\nAlkylation

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Abstract

An allylic substitution with difluoroenoxysilanes as\nthe nucleophile\nis accomplished for the enantioselective synthesis of α-allylic\nα,α-difluoroketones. With racemic branched allylic alcohols\nas the easily accessible allylic electrophile, this branched-selective\nand enantioconvergent allylic alkylation reaction is catalyzed by\nan Ir(I)/(<i>P</i>,olefin) complex and overcomes the low\nnucleophilicity of difluoroenoxysilanes to furnish β-chiral\nα,α-difluoroketones in moderate to good yields with high\nenantioselectivity (up to >99.9:0.1 er).

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Clean water and sanitation
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Mycorrhizal Fungi and Plant Interactions
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Difluoroenoxysilanes\nin Catalytic Asymmetric Allylic\nAlkylation · Figshare (2024) | TGRS Research Map | TGRS