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1 article(s) from Ji, Kegong

Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes

Kegong Ji,
Jonathan Nelson and
Liming Zhang

Beilstein J. Org. Chem. 2013, 9, 1925–1930, doi:10.3762/bjoc.9.227

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Scheme 1: Generation of α-oxo gold carbenes via intermolecular oxidation of alkynes: a non-diazo approach.

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Scheme 2: Gold-catalyzed regioselective oxidation of a sterically biased internal alkyne.

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Scheme 3: Gold-catalyzed oxidation of the propargylic acetate 4a and the mechanistic rationale.

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Scheme 4: A drastically different outcome by using diphenyl sulfoxide as the oxidant.

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Figure 1: The impact of ligands on the ratio of 5a-OAc and 5a-H in the gold-catalyzed oxidation of 4a (reacti...

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Figure 2: Natural charges at and the ¹³C chemical shifts of the alkynyl carbons in 4a.

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Published 24 Sep 2013

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