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Synfacts 2011(8): 0912-0912  
DOI: 10.1055/s-0030-1260712
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

A Mesoporous Organosilica-Supported Organocatalyst

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Heeyoel Baek
J. Y. Shi, C. A. Wang, Z. J. Li, Q. Wang, Y. Zhang, W. Wang*
Lanzhou University, P. R. of China
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

A chiral imidazolidinone catalyst (MacMillan catalyst) was supported on hollow-structured phenylene-bridged periodic mesoporous organosilica (H-PhPMO) spheres. Thus, the supported catalyst (H-PhPMO-Mac) was prepared from 1,4-bis(triethoxysilyl)benzene and trimethoxysilylpropyl azide with hematite (α-Fe2O3) nanoparticles as hard templates through condensation, etching (removal of α-Fe2O3), and Huisgen 1,3-dipolar cycloaddition. The Diels-Alder cyclo­addition of trans-cinnamaldehyde (0.25 mmol) and 1,3-cyclopentadiene (1.25 mmol) was carried out with H-PhPMO-Mac (0.05 mmol) to give 3-phenylbicyclo-[2,2,1]hept-5-ene-2-carbaldehyde in 98% yield [endo/exo = 1:1.1; 81% ee (endo) and 81% ee (exo)].