α‑Crotyl-α-difluoroboranyloxy-amides: Structure and Reactivity of Isolable Intermediates in Stereospecific α‑Ketol Rearrangements
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https://figshare.com/articles/dataset/_Crotyl_difluoroboranyloxy_amides_Structure_and_Reactivity_of_Isolable_Intermediates_in_Stereospecific_Ketol_Rearrangements/2156950
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The stereospecific BF3-mediated α-ketol rearrangement of β-hydroxy-α-ketoamides yields isolable 2-difluoroboranyloxy-3-keto-amides. X-ray and NMR analysis reveal a carbonyl coordination of the boron by the amide not the ketone. The boron complexes are air-stable solids, can be purified by silica gel chromatography, and exhibit novel reactivity in bromination and superior stereoselectivity in dipolar cycloaddition reactions.
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2016-02-13



