4.4 Article

An Improved Scalable Process for the Synthesis of (S,S)-DACH-Ph Trost Ligand

期刊

SYNLETT
卷 33, 期 13, 页码 1287-1289

出版社

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0041-1738371

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Trost ligand; DACH-Ph; coupling; 2-diphenylphosphinyl-benzoic acid; chiral diaminocyclohexane; CDI; imidazole hydrochloride; kilogram

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An improved chemical process for the synthesis of (S,S)-DACH-Ph Trost ligand has been developed. The process is simple and high-yielding, and purification can be achieved without the need for column chromatography.
An improved chemical process has been developed for the synthesis of (S,S)-DACH-Ph Trost ligand. The amidation of 2-diphenylphosphinylbenzoic acid and (S,S)-diaminocyclohexarie is promoted by stoichiometric CDI and catalytic imidazole hydrochloride. The resulting product, (S,S)-DACH-Ph Trost ligand, is isolated as a white solid in 80% yield with >99% ee by simple filtration without column chromatography. The current facile process is also demonstrated on kilogram scale.

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