期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 9, 期 -, 页码 1925-1930出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.227
关键词
enone; gold catalysis; oxidation; propargyl carboxylate
资金
- NSF [CHE-1301343]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1301343] Funding Source: National Science Foundation
Gold-catalyzed intermolecular oxidation of carboxylates of primary or secondary propargylic alcohols are realized with excellent regioselectivity, which is ascribed to inductive polarization of the C-C triple bond by the electron-withdrawing carboxy group. The gold carbene intermediates thus generated undergo selective 1,2-acyloxy migration over a 1,2-C-H insertion, and the selectivities could be dramatically improved by the use of a P,S-bidentate ligand, which is proposed to enable the formation of tris-coordinated and hence less electrophilic gold carbene species. alpha-Carboxy alpha,beta-unsaturated ketones/aldehydes can be obtained with fair to excellent yields.
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