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. 2019 May 3;9(24):13749-13756.
doi: 10.1039/c9ra01529a. eCollection 2019 Apr 30.

Lanthanide complexes combined with chiral salen ligands: application in the enantioselective epoxidation reaction of α,β-unsaturated ketones

Xuexiu Xia  1 , Chengrong Lu  1 , Bei Zhao  1   2 , Yingming Yao  1   2
Affiliations

Lanthanide complexes combined with chiral salen ligands: application in the enantioselective epoxidation reaction of α,β-unsaturated ketones

Xuexiu Xia et al. RSC Adv. .

Abstract

Readily available lanthanide amides Ln[N(SiMe3)2]3 (Ln = Nd (1), Sm (2), Eu (3), Yb (4), La (5)), combined with chiral salen ligands H2La ((S,S)-N,N'-di-(3,5-disubstituted-salicylidene)-1,2-cyclohexanediamine) and H2Lb ((S,S)-N,N'-di-(3,5-disubstituted-salicylidene)-1,2-diphenyl-1,2-ethanediamine) were employed in the enantioselective epoxidation of α,β-unsaturated ketones. It was found that the salen-La complex shows the highest efficiency and enantioselectivity. A relatively broad scope of α,β-unsaturated ketones was investigated, and excellent yields (up to 99%) and moderate to good enantioselectivities (37-87%) of the target molecules were achieved.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Chart 1
Chart 1. Epoxidation of α,β-unsaturated ketones catalyzed by complex 5a. aReactions were performed with the substrate (0.3 mmol), TBHP (0.36 mmol) in 1 mL CH3CN at −20 °C for 10 h; isolated yield; ee value were determined by chiral HPLC analysis. b15 h. c48 h.
Scheme 1
Scheme 1. The preparation of complex 8.
Scheme 2
Scheme 2. The synthesis and the molecular structure of compound 7e.
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