Published November 4, 2019
| Version v1
Journal article
Enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines: Efficient synthesis of cipargamin
Creators
- 1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology (China)
- 2. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (China)
Description
Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO-BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin. (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim)
Availability note (English)
Available from: http://dx.doi.org/10.1002/anie.201910008Additional details
Identifiers
Publishing Information
- Journal Title
- Angewandte Chemie (International Edition)
- Journal Volume
- 58
- Journal Issue
- 45
- Journal Page Range
- p. 16119-16123
- ISSN
- 1433-7851
- CODEN
- ACIEF5
INIS
- Country of Publication
- Germany
- Country of Input or Organization
- Germany
- INIS RN
- 51022788
- Subject category
- S36: MATERIALS SCIENCE; S37: INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY;
- Descriptors DEI
- AMINES; CATALYSTS; CHIRALITY; DRUGS; IMINES; LIGANDS; ORGANIC BORON COMPOUNDS; RHODIUM; SYNTHESIS
- Descriptors DEC
- ELEMENTS; METALS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; PARTICLE PROPERTIES; PLATINUM METALS; REFRACTORY METALS; TRANSITION ELEMENTS