41964-04-9Relevant articles and documents
Biocatalytic Strategy for Highly Diastereo- and Enantioselective Synthesis of 2,3-Dihydrobenzofuran-Based Tricyclic Scaffolds
Vargas, David A.,Khade, Rahul L.,Zhang, Yong,Fasan, Rudi
supporting information, p. 10148 - 10152 (2019/07/04)
2,3-Dihydrobenzofurans are key pharmacophores in many natural and synthetic bioactive molecules. A biocatalytic strategy is reported here for the highly diastereo- and enantioselective construction of stereochemically rich 2,3-dihydrobenzofurans in high enantiopurity (>99.9% de and ee), high yields, and on a preparative scale via benzofuran cyclopropanation with engineered myoglobins. Computational and structure-reactivity studies provide insights into the mechanism of this reaction, enabling the elaboration of a stereochemical model that can rationalize the high stereoselectivity of the biocatalyst. This information was leveraged to implement a highly stereoselective route to a drug molecule and a tricyclic scaffold featuring five stereogenic centers via a single-enzyme transformation. This work expands the biocatalytic toolbox for asymmetric C–C bond transformations and should prove useful for further development of metalloprotein catalysts for abiotic carbene transfer reactions.
Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C?H Activation with Silyldimesitylborane
Shishido, Ryosuke,Sasaki, Ikuo,Seki, Tomohiro,Ishiyama, Tatsuo,Ito, Hajime
supporting information, p. 12924 - 12928 (2019/11/05)
Direct dimesitylborylation of benzofuran derivatives by a C?H activation catalyzed by an iridium(I)/N-heterocyclic carbene (NHC) complex in the presence of Ph2MeSi-BMes2 afforded the corresponding dimesitylborylation products in good to high yield with excellent regioselectivity. This method provides a straightforward route to donor–(π-spacer)–acceptor systems with intriguing solvatochromic luminescence properties.
Visible light-induced monofluoromethylenation of heteroarenes with ethyl bromofluoroacetate
Yu, Wei,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 6564 - 6567 (2016/08/09)
Visible light-induced monofluoromethylenation of benzofurans and benzothiophenes with ethyl bromofluoroacetate was developed. This method provided a convenient access to novel α-fluoro-α-heteroarylesters under mild reaction conditions.