Enantiodivergent Combination of Natural Product Scaffolds Enabled by Catalytic Enantioselective Cycloaddition. Issue 27 (19th May 2016)

• Record Type: Journal Article
• Authors: Xu, Hao; Golz, Christopher; Strohmann, Carsten; Antonchick, Andrey P.; Waldmann, Herbert
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 27(2016)
• Page Start: 7761
• Page End: 7765
• Publication Date: 2016-05-19
• Subjects: asymmetric catalysis -- cycloaddition -- enantiomers -- kinetic resolution -- tropane; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201602084
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An efficient strategy has been established for the enantiodivergent synthesis of natural product inspired compounds embodying both tropane and pyrrolidine natural product fragments. This strategy includes the enantioselective kinetic resolution of racemic tropanes by means of a copper(I)‐catalyzed [3+2] cycloaddition and allows the preparation of two enantiopure products in a one‐pot reaction in high yield and with high diastereo‐ and enantioselectivity by using one chiral catalyst. Abstract : Two for one offer : An efficient method based on copper(I)‐catalyzed [3+2] cycloadditions has been developed for the enantiodivergent combination of natural product derived tropane and pyrrolidine scaffolds. The strategy enables the synthesis of two enantiopure products in a one‐pot reaction with one chiral catalyst in high diastereo‐ and enantioselectivity.