P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters

Sunewang Rixin Wang; Alexander T. Radosevich

doi:10.1021/acs.orglett.5b01784

P(NMe₂)₃-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters

Sunewang Rixin Wang
, Alexander T. Radosevich^*

^*此作品的通讯作者

Pennsylvania State University

科研成果: 期刊稿件 › 文章 › 同行评审

52 引用（Scopus）

摘要

A commercial phosphorus-based reagent (P(NMe₂)₃) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

源语言	英语
页（从-至）	3810-3813
页数	4
期刊	Organic Letters
卷	17
期	15
DOI	https://doi.org/10.1021/acs.orglett.5b01784
出版状态	已出版 - 7 8月 2015
已对外发布	是

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abstract = "A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.",

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AU - Wang, Sunewang Rixin

AU - Radosevich, Alexander T.

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N2 - A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

AB - A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

UR - https://www.scopus.com/pages/publications/84938824029

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DO - 10.1021/acs.orglett.5b01784

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AN - SCOPUS:84938824029

SN - 1523-7060

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SP - 3810

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JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters

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P(NMe₂)₃-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters