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Stereoselective Organocatalyzed Synthesis of α‐Fluorinated β‐Amino Thioesters and Their Application in Peptide Synthesis
Author(s) -
Cosimi Elena,
Engl Oliver D.,
Saadi Jakub,
Ebert MarcOlivier,
Wennemers Helma
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201607146
Subject(s) - moiety , chemistry , stereoselectivity , reagent , peptide synthesis , peptide , amino acid , combinatorial chemistry , catalysis , organocatalysis , organic chemistry , stereochemistry , enantioselective synthesis , biochemistry
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.