α‑Crotyl-α-difluoroboranyloxy-amides: Structure and Reactivity of Isolable Intermediates in Stereospecific α‑Ketol Rearrangements
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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.
创建时间：
2016-02-13
