Abstract
We developed an enantioselectively catalyzed tandem synthesis of structurally and stereochemically complex molecules that forms four carbon-carbon bonds and sets eight stereocenters with high regio-, diastereo- and enantioselectivity. It can be programmed to yield different stereoisomers by varying only the order of combination of a common set of reagents and catalysts. We report what is to our knowledge the first synthesis of both enantiomers of a chiral compound using the same chiral catalyst.
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Acknowledgements
M.P. thanks the Fonds der Chemischen Industrie for a fellowship. The research leading to these results has received funding from the European Research Council (ERC) under the European Union′s Seventh Framework Programme (FP7/2007-2013) and ERC grant agreement no. 268309.
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A.P.A. and H.W. designed experiments and supervised the project. M.P. performed experiments. M.S. and H.P. carried out the X-ray crystallographic analysis. All authors discussed the results, commented and wrote the manuscript.
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Supplementary information
Supplementary Text and Figures
Supplementary Methods and Supplementary Results (PDF 7750 kb)
Supplementary Data Set 1
Crystallographic Data for 4a (TXT 14 kb)
Supplementary Data Set 2
Crystallographic Data for 3a (TXT 21 kb)
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Potowski, M., Schürmann, M., Preut, H. et al. Programmable enantioselective one-pot synthesis of molecules with eight stereocenters. Nat Chem Biol 8, 428–430 (2012). https://doi.org/10.1038/nchembio.901
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DOI: https://doi.org/10.1038/nchembio.901
