TY - JOUR
T1 - Amphiphilic immobilized diphenylprolinol alkyl ether catalyst on PS-PEG resin
AU - Koshino, Seitaro
AU - Hattori, Shusuke
AU - Hasegawa, Shota
AU - Haraguchi, Naoki
AU - Yamamoto, Takeshi
AU - Suginome, Michinori
AU - Uozumi, Yasuhiro
AU - Hayashi, Yujiro
N1 - Funding Information:
This research was supported by Joint Research by Institute for Molecular Science (IMS). (IMS program No. 207). This work was supported by JSPS KAKENHI Grant Number JP18H04380 and JP19H05630.
Publisher Copyright:
© 2021 The Chemical Society of Japan.
PY - 2021
Y1 - 2021
N2 - Diphenylprolinol silyl ether is a widely used organocatalyst, and its immobilization on a solid support was investigated for the easy recycling and reuse of this catalyst. Because a silyl ether bond of the catalyst is weak, its alkyl ether was attached to polymers such as a polyquinoxaline-based polymer, a polystyrene polymer (PS) resin, and a polystyrenepoly(ethylene glycol) graft copolymer (PS-PEG) resin. Although a polymer-supported organocatalyst generally decreases its reactivity compared with the monomer catalyst, diphenylprolinol anthrylmethyl ether supported on PS-PEG was found to be a reactive organocatalyst; it catalyzed the Michael reaction of an aldehyde and a nitroalkene in water without an organic solvent being present, with excellent diastereo- and enantioselectivities.
AB - Diphenylprolinol silyl ether is a widely used organocatalyst, and its immobilization on a solid support was investigated for the easy recycling and reuse of this catalyst. Because a silyl ether bond of the catalyst is weak, its alkyl ether was attached to polymers such as a polyquinoxaline-based polymer, a polystyrene polymer (PS) resin, and a polystyrenepoly(ethylene glycol) graft copolymer (PS-PEG) resin. Although a polymer-supported organocatalyst generally decreases its reactivity compared with the monomer catalyst, diphenylprolinol anthrylmethyl ether supported on PS-PEG was found to be a reactive organocatalyst; it catalyzed the Michael reaction of an aldehyde and a nitroalkene in water without an organic solvent being present, with excellent diastereo- and enantioselectivities.
KW - Asymmetric reaction
KW - Organocatalyst
KW - Polymer-supported catalyst
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U2 - 10.1246/BCSJ.20200355
DO - 10.1246/BCSJ.20200355
M3 - Review article
AN - SCOPUS:85103879241
SN - 0009-2673
VL - 94
SP - 790
EP - 797
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 3
ER -