From the roots of Campylotropis hirtella (Franch.) Schindl., many natural dihydroflavonol compounds have been extracted, and they possess a structurally novel feature of chiral tertiary alcohol groups. However, the content of the compounds in the plant is extremely low. At this point, to satisfy the needs of further experimental research on these compounds, much effort has been invested in the chemical synthesis of the core structure of 3-hydroxy-3-phenylchroman-4-one. This study aimed to explore a novel method for the synthesis of dihydroflavonol (3), and its application in the production of a natural product (14). The method started with commercially available materials, and provided a foundation for total synthesis of natural compounds of dihydroflavonol.
Palladium-catalyzed C-H activation reactions have attracted the attention of organic researchers due to their unique high selectivity, broad functional group tolerance, and high efficiency, and they are widely used in natural products and asymmetric synthesis. Here, we report an example of enantioselective C-H alkenylation between β-alkyl phenylethylamine compounds and styrenes with Boc-L-lle-OH as the ligand and nosylamide as the directing group. This reaction is applicable to styrene containing various electron-deficient and electron-donating substitutions and may be utilized for the synthesis of benzoazepine compounds.
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