Side-arm-promoted highly enantioselective ring-opening reactions and kinetic resolution of donor-acceptor cyclopropanes with amines

Journal of the American Chemical Society
You-Yun ZhouYong Tang

Abstract

A Ni-catalyzed asymmetric ring-opening reaction of 2-substituted cyclopropane-1,1-dicarboxylates with aliphatic amines has been accomplished using the chiral indane-trisoxazoline (In-TOX) ligand. This highly enantioselective reaction provides an efficient approach to a variety of chiral γ-substituted γ-amino acid derivatives, which are readily transformed into multifunctionalized piperidines and γ-lactams. The single-crystal X-ray structure of the TOX-Ni complex is provided, and the role of the side arm in the chiral ligand is discussed.

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Citations

Nov 6, 2015·Journal of the American Chemical Society·Qi-Kai KangYong Tang
Aug 8, 2015·Organic Letters·Qiong-Jie LiuYong Tang
Dec 22, 2016·Journal of the American Chemical Society·Wei DingWen-Jing Xiao
Apr 7, 2017·Nature Communications·Yoshihiro SohtomeMikiko Sodeoka
Apr 16, 2014·Journal of the American Chemical Society·Florian de NanteuilJerome Waser
May 26, 2016·Organic & Biomolecular Chemistry·Xuan FuXiaoming Feng
Apr 3, 2015·Organic & Biomolecular Chemistry·Ren-Rong LiuYi-Xia Jia
Jan 13, 2015·Chemical Communications : Chem Comm·Hong-Ying NiuHai-Ming Guo
May 10, 2018·Angewandte Chemie·Alesandere OrtegaJose L Vicario
Jul 9, 2016·Angewandte Chemie·Trinadh KaicharlaAkkattu T Biju
Jun 28, 2014·Chemical Communications : Chem Comm·F de NanteuilJ Waser
Jul 20, 2017·Angewandte Chemie·Saikat DasArmido Studer
Nov 1, 2018·ChemPlusChem·Silvia González-Pelayo, Luis A López
Aug 1, 2013·Chemical Communications : Chem Comm·Olga A IvanovaMikhail Ya Melnikov
Nov 17, 2020·Angewandte Chemie·Yong XiaXiaoming Feng
Jan 13, 2021·Angewandte Chemie·Ivan A AndreevIgor V Trushkov
Dec 30, 2014·Organic Letters·Alexander J CraigBill C Hawkins
Jun 13, 2015·Journal of the American Chemical Society·Hao XuYong Tang
Jul 3, 2013·Organic Letters·Florian de NanteuilJérôme Waser
May 9, 2013·Journal of the American Chemical Society·Hu XiongYong Tang

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