期刊
ORGANIC LETTERS
卷 13, 期 11, 页码 2830-2833出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol200784y
关键词
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资金
- NIH [R01 GM67163]
- Abbott Laboratories
- NSF [TG-CHE-070040]
Enantioselective intramolecular oxidative amidation of alkenes has been achieved using a (pyrox)Pd(II)(TFA)(2) catalyst (pyrox = pyridine-oxazoline, TFA = trifluoroacetate) and 02 as the sole stoichiometric oxidant. The reactions proceed at room temperature in good-to-excellent yields (58-98%) and with high enantioselectivity (ee = 92-98%). Catalyst-controlled stereoselective cyclization reactions are demonstrated for a number of chiral substrates. DFT calculations suggest that the electronic asymmetry of the pyrox ligand synergizes with steric asymmetry to control the stereochemical outcome of the key amidopalladation step.
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