Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds
Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds
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DOI：
10.1021/acscatal.8b04516
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发表时间：
2018-11
期刊：
影响因子：
12.9
通讯作者：
Vincent van der Puyl;J. Derosa;K. Engle
中科院分区：
文献类型：
--
作者：
Vincent van der Puyl;J. Derosa;K. Engle
本文报道了非共轭烯基羰基化合物与邻苯甲酰基羟胺（N-O）亲电试剂和芳基/烷基锌亲核试剂的区域选择性镍催化顺式1，2-碳胺化反应，得到β-和γ-氨基酸衍生物。该方法能够制备含有结构上不同的叔胺基序（包括杂环）的产物，并且还可以用于形成季碳中心。该反应利用了一个8-氨基喹啉导向基团来控制区域化学反应的结果，并抑制了N-O亲电试剂和有机锌亲核试剂之间的双组分偶联。
We report a regioselective, nickel-catalyzed syn-1,2-carboamination of non-conjugated alkenyl carbonyl compounds with O-benzoyl hydroxylamine (N–O) electrophiles and aryl/alkylzinc nucleophiles to afford β- and γ-amino acid derivatives. This method enables preparation of products containing structurally diverse tertiary amine motifs, including heterocycles, and can also be used to form quaternary carbon centers. The reaction takes advantage of a tethered 8-aminoquinoline directing group to control the regiochemical outcome and suppress two-component coupling between the N–O electrophile and organozinc nucleophile.