TY - JOUR
T1 - Synthesis, Resolution, and Absolute Configuration of Chiral Tris(2-pyridylmethyl)amine-Based Hemicryptophane Molecular Cages
AU - Zhang, Dawei
AU - Bousquet, Benjamin
AU - Mulatier, Jean Christophe
AU - Pitrat, Delphine
AU - Jean, Marion
AU - Vanthuyne, Nicolas
AU - Guy, Laure
AU - Dutasta, Jean Pierre
AU - Martinez, Alexandre
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/6/16
Y1 - 2017/6/16
N2 - The synthesis, characterization, and chiroptical properties of a new class of hemicryptophane cages combining a cyclotriveratrylene unit and a tris(2-pyridylmethyl)amine (TPA) moiety are reported. Changing the linkers between these two units allows for the modification of the size and shape of the cavity. The synthesis is straightforward and efficient, providing gram-scale of cage compounds. The racemic mixture of each hemicryptophane host can be readily resolved by chiral HPLC, giving an easy access to the enantiopure molecular cages of which absolute configurations have been assigned by ECD spectroscopy. These new hemicryptophanes are available chemical platforms ready to use for various purposes due to the versatile metal complexation properties of the TPA unit. A Zn(II)@hemicryptophane complex has been obtained and used as a heteroditopic host for the selective recognition of zwitterionic guests.
AB - The synthesis, characterization, and chiroptical properties of a new class of hemicryptophane cages combining a cyclotriveratrylene unit and a tris(2-pyridylmethyl)amine (TPA) moiety are reported. Changing the linkers between these two units allows for the modification of the size and shape of the cavity. The synthesis is straightforward and efficient, providing gram-scale of cage compounds. The racemic mixture of each hemicryptophane host can be readily resolved by chiral HPLC, giving an easy access to the enantiopure molecular cages of which absolute configurations have been assigned by ECD spectroscopy. These new hemicryptophanes are available chemical platforms ready to use for various purposes due to the versatile metal complexation properties of the TPA unit. A Zn(II)@hemicryptophane complex has been obtained and used as a heteroditopic host for the selective recognition of zwitterionic guests.
UR - https://www.scopus.com/pages/publications/85020904467
U2 - 10.1021/acs.joc.7b00559
DO - 10.1021/acs.joc.7b00559
M3 - 文章
C2 - 28481535
AN - SCOPUS:85020904467
SN - 0022-3263
VL - 82
SP - 6082
EP - 6088
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 12
ER -