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Large‐Scale Synthesis of Symmetric Tetramine Ligands by Using a Modular Double Reductive Amination Approach
Author(s) -
Tretbar Maik,
Stark Christian B. W.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700772
Subject(s) - tetramine , reductive amination , chemistry , combinatorial chemistry , amination , modular design , sequence (biology) , catalysis , organic chemistry , computer science , biochemistry , operating system
Tetramine ligands play an important role in a broad range of transition metal catalyzed transformations. We here present a flexible and modular approach to this class of ligands using a double reductive amination strategy. Thus, the target molecules were prepared in a highly efficient manner in only three steps, from commercially available starting materials. Excellent overall yields, of up to 96 % were reached. Notably, chiral C 2 ‐symmetric ligands are available using this procedure. All reactions are easily scalable and the tetramine ligands were obtained in excellent purity, while only a single chromatographic purification is required at the end of the three step sequence.