期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 10, 页码 3410-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja808959e
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We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to alpha,alpha-arylated secondary or tertiary alcohols. We also report density functional theory calculations supporting the proposal that arylation proceeds through a dearomatizing attack on the aromatic ring, a significantly lower energy pathway than the 1,2-acyl transfer observed with related N-alkyl carbamates.
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