TY - JOUR
T1 - Site-Selective and Stereoselective C-H Functionalization of N-Cyclopropylamides via a Directed Remote Metalation Strategy
AU - Ermolovich, Yuri
AU - Barysevich, Maryia V.
AU - Adamson, Jasper
AU - Rogova, Oksana
AU - Kaabel, Sandra
AU - Järving, Ivar
AU - Gathergood, Nicholas
AU - Snieckus, Victor
AU - Kananovich, Dzmitry G.
N1 - Publisher Copyright:
© Copyright 2019 American Chemical Society.
PY - 2019/2/15
Y1 - 2019/2/15
N2 - A new methodology for site-selective and stereoselective C-H functionalization of aminocyclopropanes via directed remote lithiation has been developed. Treatment of N-directing group (DG = pivaloyl, tetramethylsuccinimidoyl) arylcyclopropanes with t-BuLi results in a clean β-lithiation and, following quench with electrophiles, leads to a range of cyclopropane derivatives. Sequential double lithiation-methylation to give a dimethylated cyclopropane has been achieved. X-ray, NMR, and computational studies allow rationalization of syn-DG β-deprotonation selectivity via a DG-lithium base coordinated complex.
AB - A new methodology for site-selective and stereoselective C-H functionalization of aminocyclopropanes via directed remote lithiation has been developed. Treatment of N-directing group (DG = pivaloyl, tetramethylsuccinimidoyl) arylcyclopropanes with t-BuLi results in a clean β-lithiation and, following quench with electrophiles, leads to a range of cyclopropane derivatives. Sequential double lithiation-methylation to give a dimethylated cyclopropane has been achieved. X-ray, NMR, and computational studies allow rationalization of syn-DG β-deprotonation selectivity via a DG-lithium base coordinated complex.
UR - http://www.scopus.com/inward/record.url?scp=85061234275&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.8b03955
DO - 10.1021/acs.orglett.8b03955
M3 - Article
C2 - 30715898
AN - SCOPUS:85061234275
VL - 21
SP - 969
EP - 973
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 4
ER -