TY - JOUR
T1 - Enantioselective synthesis of planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites and their use as chiral ligands
AU - Hazra, Madhurima
AU - Kanyiva, Kyalo Stephen
AU - Shibata, Takanori
N1 - Funding Information:
This work was supported by JST , ACT-C , Japan. We are grateful to Tokyo Chemical Industry Co., Ltd. (TCI) for generously supplying 1,11-dioxa[11]paracyclophane.
Publisher Copyright:
© 2016 Elsevier Ltd
PY - 2016
Y1 - 2016
N2 - A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained.
AB - A library of bench-stable planar-chiral 1,11-dioxa[11]paracyclophane-derived phosphoramidites was synthesized by a three step procedure: enantioselective ortho-lithiation, reductive amination and coupling with phosphorochloridites. The efficacy of these phosphoramidite as chiral ligands was tested in the Pd-catalyzed allylic alkylation of dimethyl malonate and the Cu-catalyzed ethylation of chalcone under the reported conditions, with moderate enantioselectivity being obtained.
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U2 - 10.1016/j.tetasy.2016.08.015
DO - 10.1016/j.tetasy.2016.08.015
M3 - Article
AN - SCOPUS:84989849562
SN - 0957-4166
VL - 27
SP - 1081
EP - 1087
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 20-21
ER -