Key Laboratory of Functional Molecular Solids (Ministry of Education), Anhui Key Laboratory of Molecular Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.
Org Lett. 2022 Jul 22;24(28):5143-5148. doi: 10.1021/acs.orglett.2c01981. Epub 2022 Jul 10.
Herein, we present the Pd(II)-catalyzed atroposelective C-H acyloxylation strategy for the assembly of biaryl aldehyde atropoisomers using readily available amino acids as the catalytic auxiliary and chiral pool. This strategy exhibits a broad substrate scope with a good yield (≤90%) and excellent enantioselectivity (≤99%), furnishing functionalized aldehydes through direct asymmetric C-H oxidation. The application utility of this method was demonstrated by the concise synthesis of a kind of atropoisomeric amino-phenol organocatalyst, which enables good enantiocontrol in catalyzing asymmetric addition of diethylzinc to aldehydes.
在此，我们提出了一种 Pd(II)催化的手性选择性 C-H 酰氧基化策略，用于使用易得的氨基酸作为催化辅助剂和手性库来构建联芳基醛的对映异构体。该策略具有广泛的底物范围，收率高（≤90%），对映选择性好（≤99%），通过直接不对称 C-H 氧化提供功能化醛。该方法的应用实用性通过一种对映异构氨基酸-苯酚有机催化剂的简洁合成得到了证明，该催化剂在手性控制催化二乙基锌与醛的不对称加成方面表现出良好的效果。
