Asymmetric Catalysis with MOFs Prepared via Chiral Induction
Effect

doi:10.1055/s-0030-1259143

Synfacts 2011(1): 0105-0105
DOI: 10.1055/s-0030-1259143

Polymer-Supported Synthesis

Asymmetric Catalysis with MOFs Prepared via Chiral Induction Effect

Rezensent(en):Yasuhiro Uozumi, Yoichi M. A. Yamada, Yoshinari Yuyama

D. Dang, P. Wu, C. He, Z. Xie, C. Duan*
Dalian University of Technology, P. R. of China
Homochiral Metal-Organic Frameworks for Heterogeneous Asymmetric Catalysis
J. Am. Chem. Soc. 2010, 132: 14321-14323

Abstract

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Key words

homochiral metal-organic frameworks - cyanosilylation - cerium

Significance

Homochiral metal-organic frameworks (MOFs) were prepared through the chiral induction effect. Thus, the homochiral crystallization of Ce(NO₃)˙6H₂O and H₄MDIP was performed with l- or d-BCIP as chiral inducers in water to give Ce-MDIP1 and Ce-MDIP2 (where no BCIP was installed), which exhibited Cotton effects exactly opposite to each other. Ce-MDIPs promoted the cyanosilylation to give the corresponding cyanohydrin derivatives quantitatively with 93 to >98% ee.

Comment

Ce-MDIP1 was reused twice without significant loss of catalytic activity. Cd-TBT was also prepared from Cd(ClO₄)˙6H₂O and H₃TBT under similar conditions. Cd-TBT mediated the direct aldol reaction of aldehydes and cyclohexanone to afford the corresponding β-hydroxy ketones in 8-97% yield with 58-61% ee in ten days.

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