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

Sunewang Rixin Wang and Alexander T. Radosevich*

*Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States, Email: radosevichpsu.edu

S. R. Wang, A. T. Radosevich, Org. Lett., 2015, 17, 3810-3813.

DOI: 10.1021/acs.orglett.5b01784


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Abstract

P(NMe2)3 mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides via a two-electron redox addition of the tricoordinate phosphorus reagent to the α-keto ester compound (Kukhtin-Ramirez addition). Depending on the work-up conditions, either Barbier-type addition or ylide-free olefination products can be isolated.

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Key Words

α,β-unsaturated esters, tris(dimethylamino)phosphine


ID: J54-Y2015