TY - JOUR
T1 - Equilibrium shift induced by chiral nanoparticle precipitation in rhodium-catalyzed disulfide exchange reaction
AU - Miyagawa, Masamichi
AU - Arisawa, Mieko
AU - Yamaguchi, Masahiko
N1 - Funding Information:
Financial support from JSPS (No. 25249108 ) is acknowledged. M.A. expresses her appreciation to the financial support provided by Grants-in-Aid for Scientific Research (Nos. 25109503 and 15H00911 ) and the Asahi Glass Foundation . M.M. acknowledges a fellowship from the Japan Society for Young Japanese Scientists (No. 25-7469).
Publisher Copyright:
© 2015 Elsevier Ltd.All rights reserved.
PY - 2015/6/18
Y1 - 2015/6/18
N2 - Chiral silica (P)-nanoparticles grafted with (P)-helicene recognize the molecular structure of a chiral diol disulfide in the presence of monool disulfide and dibutyl disulfide. The (P)-nanoparticles selectively adsorb the diol disulfide, aggregate, and precipitate from solution. Under rhodium-catalyzed equilibrium among three disulfides, the diol disulfide is removed from solution by precipitation, which induces an equilibrium shift in the solution. By conducting the precipitation experiment twice, we obtained the diol disulfide in 37% yield from a statistical 1:2:1 equilibrium mixture of three disulfides. The method is applied to a racemic monool disulfide, and an optically active diol disulfide is obtained via kinetic resolution and equilibrium shift.
AB - Chiral silica (P)-nanoparticles grafted with (P)-helicene recognize the molecular structure of a chiral diol disulfide in the presence of monool disulfide and dibutyl disulfide. The (P)-nanoparticles selectively adsorb the diol disulfide, aggregate, and precipitate from solution. Under rhodium-catalyzed equilibrium among three disulfides, the diol disulfide is removed from solution by precipitation, which induces an equilibrium shift in the solution. By conducting the precipitation experiment twice, we obtained the diol disulfide in 37% yield from a statistical 1:2:1 equilibrium mixture of three disulfides. The method is applied to a racemic monool disulfide, and an optically active diol disulfide is obtained via kinetic resolution and equilibrium shift.
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U2 - 10.1016/j.tet.2015.05.106
DO - 10.1016/j.tet.2015.05.106
M3 - Article
AN - SCOPUS:84931009968
SN - 0040-4020
VL - 71
SP - 4920
EP - 4926
JO - Tetrahedron
JF - Tetrahedron
IS - 30
ER -