铑(III)催化的烯烃不对称 1,2-碳酰胺化反应可获得手性 2,3-二氢-3-苯并呋喃甲酰胺。
Rhodium(III)-Catalyzed Asymmetric 1,2-Carboamidation of Alkenes Enables Access to Chiral 2,3-Dihydro-3-benzofuranmethanamides.
机构信息
Department of Medicinal Chemistry, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
出版信息
Org Lett. 2022 Mar 11;24(9):1762-1767. doi: 10.1021/acs.orglett.2c00029. Epub 2022 Mar 2.
Through the initial screening and further rational design of chiral cyclopentadienyl ligands, a chiral rhodium-catalyzed enantioselective 1,2-carboamidation of aromatic tethered alkenes was developed, enabling the asymmetric preparation of various chiral 2,3-dihydro-3-benzofuranmethanamides with an enantioenriched all-carbon quaternary center at the β position of amide. This robust transformation has a broad functional group tolerance, excellent enantioselectivities (up to 98.5:1.5 er), and a mild reaction conditions, releasing CO as the single byproduct.
通过对手性环戊二烯基配体的初步筛选和进一步的合理设计，开发了一种手性铑催化的对映选择性 1,2-碳酰胺化反应，可不对称制备各种手性 2,3-二氢-3-苯并呋喃甲酰胺，其中酰胺的β位具有富集的全碳季碳中心。该反应条件温和，以 CO 为唯一副产物，具有广泛的官能团耐受性，优异的对映选择性（高达 98.5:1.5 er）。
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