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

Title: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

Volume: 15 Issue: 11

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

Affiliation:

• Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh,India

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

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.

Cite this article as:

Patel Deepak , Thakur Singh Santosh *, Shinde S. Sandip and Kumar Pradeep , 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, Letters in Organic Chemistry 2018; 15 (11) . https://dx.doi.org/10.2174/1570178615666171212144938