通过氮杂-Heck反应合成仲不饱和内酰胺
Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.
作者信息
Shuler Scott A, Yin Guoyin, Krause Sarah B, Vesper Caroline M, Watson Donald A
机构信息
Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
出版信息
J Am Chem Soc. 2016 Oct 26;138(42):13830-13833. doi: 10.1021/jacs.6b08932. Epub 2016 Oct 18.
Abstract
The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.
摘要
报道了通过钯催化的O-苯基异羟肟酸酯与侧链烯烃环化制备不饱和仲内酰胺的方法。该方法能够快速获得多种内酰胺，这些内酰胺是生物碱合成中广泛使用的有用砌块。机理研究支持氮杂Heck型反应途径。
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2
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3
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6
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7
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8
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