Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines

Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines
Luis Miguel Barrera Arbelaez, L. Reginald Mills, Sophie A. L. Rousseaux
Metal homoenolates, produced via C–C bond cleavage of cyclopropanols, have been extensively investigated as nucleophiles for the synthesis of β-substituted carbonyl derivatives. Herein, we demonstrate that zinc homoenolates can react as carbonyl-electrophiles in the presence of nucleophilic amines to yield highly valuable trans-cyclopropylamines in good yields and high diastereoselectivities. GSK2879552, a lysine demethylase 1 inhibitor currently in clinical trials for the treatment of small cell lung carcinoma, was synthesized using this strategy.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07104

DOI: 10.1021/jacs.7b07104

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