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Yolk-Shell-Mesostructured Silica-Supported Dual Molecular Catalyst for Enantioselective Tandem Reactions

Yolk-Shell-Mesostructured Silica-Supported Dual Molecular Catalyst for Enantioselective Tandem Reactions

Liang Wu, Yilong Li, Jingjing Meng, Ronghua Jin, Jingrong Lin, Guohua Liu

Chempluschem. 2018 Sep;83(9):861-867.

PMID: 31950681

Abstract:

Yolk-shell-mesostructured silica was used as a support in the development of an active-site-isolated bifunctional catalyst that can mediate a sequential organic transformation. Herein, through immobilization, the location of two catalytic species is controlled: a base functionality is anchored in the channels of the outer silica shell and a chiral ruthenium/diamine functionality is anchored on the inner silica yolk. The result is a yolk-shell-mesostructured silica-supported active-site-isolated dual molecule catalyst. Structural analysis through solid-state carbon 13 C NMR spectroscopy reveals its well-defined single-site dual active centers. Electron microscopy investigations disclose its uniformly distributed mesoporous nanoparticles. As envisaged, this bifunctional catalyst enables a controllable aza-Michael addition/asymmetric transfer hydrogenation catalytic sequence, where the base-catalyzed aza-Michael addition of enones and amines to aryl-substituted β -secondary amino ketones is followed by a Ru-catalyzed asymmetric transfer hydrogenation. Various aryl-substituted γ-secondary amino alcohols are obtained in high yields and enantioselectivities via this one-pot enantioselective organic transformation. Furthermore, the heterogeneous catalyst can be applied in a continuous-flow process, which was shown to be particularly attractive for the practical preparation of aryl-substituted γ-secondary amino alcohols in an environmentally friendly medium.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7631869-A	Silica, mesostructured		7631-86-9	Price

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