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Direct and quantitative monitoring of catalytic organic reactions under heterogeneous conditions using direct analysis in real time mass spectrometry.
Chem Sci
April 2020
Department of Chemistry, School of Science, The University of Tokyo. Hongo Bunkyo-ku Tokyo 113-0033 Japan
This new method overcomes problems of conventional analytical methodologies such as light scattering and sampling reproducibility issues. We used this method for mechanistic studies of catalytic reactions under heterogeneous conditions. Direct-type hydroxymethylation reactions and Mukaiyama-type hydroxymethylation reactions both catalyzed by a scandium-bipyridine ligand complex under micellar conditions were employed as examples of heterogeneous reactions.
View Article and Find Full Text PDFTotal synthesis of (+)-isatisine a: application of a silicon-directed mukaiyama-type [3 + 2]-annulation.
J Org Chem
March 2015
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
Complete details of an asymmetric synthesis of (+)-isatisine A (1) are described. The synthesis highlights the use of a highly diastereoselective Mukaiyama-type [3 + 2]-annulation of allylsilane 5 with the unsaturated aldehyde 9a to assemble the functionalized tetrahydrofuran core of isatisine A. A convergent route to the framework of the natural product was established that employed a substrate-controlled indole coupling that was followed by a late-stage intramolecular copper(I)-mediated amidation to complete the assembly of the tetracyclic framework of (+)-isatisine A.
View Article and Find Full Text PDFTowards direct Mukaiyama-type reactions catalytic in silicon.
Angew Chem Int Ed Engl
September 2011
Departamento de Química Aplicada, Universidad Pública de Navarra, Campus de Arrosadía, 31006 Pamplona, Spain.
Total synthesis of (+)-isatisine A.
Org Lett
February 2011
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Total synthesis of (+)-isatisine A is described based on the application of a silyl-directed Mukaiyama-type [3 + 2]-annulation for the preparation of a fully substituted furan core. The indole branch forming the quaternary carbon center at C2 was constructed by addition to an intermediate N-acyliminium ion derived from aminal 4. In addition, the fused tetracyclic framework including furan core was built up using modified Buchwald amidation conditions.
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