连续烯丙基 C-H 胺化/乙烯基 C-H 芳基化：一种从α-烯烃合成非天然氨基酸的策略。
Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.
机构信息
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
出版信息
Org Lett. 2012 Mar 16;14(6):1386-9. doi: 10.1021/ol300063t. Epub 2012 Feb 24.
Abstract
Tandem reaction sequences that selectively convert multiple C-H bonds of abundant hydrocarbon feedstocks to functionalized materials enable rapid buildup of molecular complexity in an economical way. A tandem C-H amination/vinylic C-H arylation reaction sequence is described under Pd(II)/sulfoxide-catalysis that furnishes a wide range of α- and β-homophenylalanine precursors from commodity α-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and densely functionalized homophenylalanine derivatives are demonstrated.
摘要
串联反应序列可选择性地将丰富烃原料的多个 C-H 键转化为功能材料，从而以经济的方式快速构建分子复杂性。本文描述了在 Pd(II)/亚砜催化下的串联 C-H 胺化/乙烯基 C-H 芳基化反应序列，该序列可从商品α-烯烃和易得的芳基硼酸中提供广泛的α-和β-同型苯丙氨酸前体。展示了获得对映纯氨基酸酯和稠合功能化同型苯丙氨酸衍生物的一般途径。
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