Catalytic and Efficient Synthesis of Optically Active Terminal Epoxides and 1,2-Diols using a New Lanthanum Triflate Assisted C1-Symmetric Bimetallic Chiral Salen Cobalt Complex

Author(s): Deepak Patel, Santosh Singh Thakur*, Sandip S. Shinde, Pradeep Kumar.

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 11 , 2018

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Abstract:

The catalytic asymmetric synthesis of terminal epoxides and 1,2-diols via a hydrolytic kinetic resolution of racemic terminal epoxides using a new bimetallic chiral salen CoIII complex incorporated with La(OTf)3 as a catalyst is reported. The new bimetallic chiral salen CoIII complex bearing La(OTf)3 was prepared in a one-pot procedure by activation and bimetallic complex formation from the inactive Jacobsen chiral salen CoII complex (salen = N, N′-bis(3,5-di-tert-butylsalicylidene)-1,2- cyclohexane-diamine). We observed that C1-symmetric chiral bimetallic Co-complex coordinated with La(OTf)3 works as a chiral catalyst and remarkably increased the reactivity and enantioselectivity in the hydrolytic kinetic resolution of terminal epoxides compared to its monometallic analogues. La(OTf)3 plays a crucial role as an achiral Lewis acid in this process, which is supported by the experimental observation presented. To explore the absolute configuration of glycidyl butyrate a vibrational circular dichroism (VCD) spectra was calculated using density functional theory.

Keywords: Chiral epoxides, asymmetric catalysis, bimetallic chiral salen complex, hydrolytic kinetic resolution, lewis acid, VCD.

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Article Details

VOLUME: 15
ISSUE: 11
Year: 2018
Page: [960 - 966]
Pages: 7
DOI: 10.2174/1570178615666171212144938
Price: $58

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