Electrophilic
Zinc Homoenolates: Synthesis of Cyclopropylamines
from Cyclopropanols and Amines
L. Reginald Mills
Luis Miguel Barrera Arbelaez
Sophie A. L. Rousseaux
10.1021/jacs.7b07104.s001
https://acs.figshare.com/articles/journal_contribution/Electrophilic_Zinc_Homoenolates_Synthesis_of_Cyclopropylamines_from_Cyclopropanols_and_Amines/5311381
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 <i>trans-</i>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.
2017-08-15 13:18:12
cyclopropylamine
presence
lysine demethylase 1 inhibitor
GSK
strategy
carbonyl-electrophile
diastereoselectivitie
nucleophilic amines
carbonyl derivatives
Cyclopropanol
synthesis
Electrophilic Zinc Homoenolates
β-
nucleophile
cyclopropanol
zinc homoenolates
Cyclopropylamine
tran
cell lung carcinoma
Herein
yield
cleavage
Synthesi
Amines Metal homoenolates
bond