Synthesis of Chiral Functionalised Cyclobutylpyrrolidines and Cyclobutylamino Alcohols from (-)-(S)-Verbenone - Applications in the Stabilisation of Ruthenium Nanocatalysts

Stereoselective and efficient synthetic routes to pyrrolidines and amino alcohols anchored to chiral polysubstituted cyclobutane moieties have been developed from (–)‐(S)‐verbenone. These original frameworks, in particular the diamines and amino alcohols, are appropriate stabilisers of metallic nanoparticles, especially for the synthesis of ruthenium nanomaterials, which found catalytic applications in the hydrogenation of arenes and nitrobenzene derivatives to afford selectively the corresponding cyclohexane or aniline derivatives. Pyrrolidines and amino alcohols anchored to chiral polysubstituted cyclobutane moieties are synthesised stereoselectively from (–)‐verbenone. Some of them are appropriate stabilisers of ruthenium nanoparticles and find catalytic applications in the hydrogenation of arenes and nitrobenzene derivatives to afford selectively the corresponding cyclohexane or aniline derivatives.