Jump to main content
Jump to site search

Issue 9, 2012
Previous Article Next Article

Promoted activity of Cr(Salen) in a nanoreactor for kinetic resolution of terminal epoxides

Author affiliations

Abstract

Cr(Salen) catalyzed kinetic resolution of terminal epoxides via asymmetric ring opening (ARO) with TMSN3 is an important approach for the synthesis of enantiopure 1,2-amino alcohols, however, the high catalyst usage amount (1–2 mol%) impedes its practical applications. An efficient solid nanoreactor was constructed by encapsulation of Cr(Salen) and pyridine in the nanocages of mesoporous silica. This solid nanoreactor exhibits high activity (TOF: 1325 h−1) and high enantioselectivity (91% ee) for the kinetic resolution of 1,2-epoxyhexane via ARO with TMSN3 at a catalyst concentration as low as 0.002 mol%, whereas the homogeneous counterpart affords almost no conversion of epoxide under similar reaction conditions. The high activity of the solid nanoreactor is mainly attributed to the greatly intensified cooperative activation in the nanocages as evidenced by the sharply increased TOF in parallel with Cr(Salen) concentration in each nanocage. The increased nucleophilicity of Cr(Salen) after coordination to pyridine could also promote the catalytic activity. The solid nanoreactor can be easily separated and recycled. We demonstrated the possibility for designing an efficient solid nanoreactor for asymmetric catalysis by taking the advantages of the cooperative activation.

Graphical abstract: Promoted activity of Cr(Salen) in a nanoreactor for kinetic resolution of terminal epoxides

Back to tab navigation

Supplementary files

Publication details

The article was received on 23 May 2012, accepted on 20 Jun 2012 and first published on 21 Jun 2012


Article type: Edge Article
DOI: 10.1039/C2SC20653F
Citation: Chem. Sci., 2012,3, 2864-2867
  •   Request permissions

    Promoted activity of Cr(Salen) in a nanoreactor for kinetic resolution of terminal epoxides

    S. Bai, B. Li, J. Peng, X. Zhang, Q. Yang and C. Li, Chem. Sci., 2012, 3, 2864
    DOI: 10.1039/C2SC20653F

Search articles by author

Spotlight

Advertisements