ja7b07104_si_001.pdf (15.14 MB)
Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines
journal contribution
posted on 2017-08-15, 13:18 authored by L. Reginald Mills, Luis Miguel Barrera Arbelaez, Sophie A. L. RousseauxMetal 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.
History
Usage metrics
Categories
Keywords
cyclopropylaminepresencelysine demethylase 1 inhibitorGSKstrategycarbonyl-electrophilediastereoselectivitienucleophilic aminescarbonyl derivativesCyclopropanolsynthesisElectrophilic Zinc Homoenolatesβ-nucleophilecyclopropanolzinc homoenolatesCyclopropylaminetrancell lung carcinomaHereinyieldcleavageSynthesiAmines Metal homoenolatesbond
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC