Stereoselective Organocatalyzed Synthesis of α‐Fluorinated β‐Amino Thioesters and Their Application in Peptide Synthesis |
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Authors: | Dr Jakub Saadi Dr Marc‐Olivier Ebert Prof Dr Helma Wennemers |
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Institution: | ETH Zürich, Laboratory for Organic Chemistry, D-CHAB, Zürich, Switzerland |
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Abstract: | α‐Fluorinated β‐amino thioesters were obtained in high yields and stereoselectivities by organocatalyzed addition reactions of α‐fluorinated monothiomalonates (F‐MTMs) to N‐Cbz‐ and N‐Boc‐protected imines. The transformation requires catalyst loadings of only 1 mol % and proceeds under mild reaction conditions. The obtained addition products were readily used for coupling‐reagent‐free peptide synthesis in solution and on solid phase. The α‐fluoro‐β‐(carb)amido moiety showed distinct conformational preferences, as determined by crystal structure and NMR spectroscopic analysis. |
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Keywords: | cinchona alkaloids fluorine organocatalysis thioesters β -amino acids |
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