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Synfacts 2011(1): 0105-0105  
DOI: 10.1055/s-0030-1259143
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Catalysis with MOFs Prepared via Chiral Induction Effect

Contributor(s):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  
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Publication History

Publication Date:
21 December 2010 (online)

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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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