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

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.

SUBMITTER: Xia X 

PROVIDER: S-EPMC9063913 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Xia Xuexiu X   Lu Chengrong C   Zhao Bei B   Yao Yingming Y  

RSC advances 20190401 24

Readily available lanthanide amides Ln[N(SiMe<sub>3</sub>)<sub>2</sub>]<sub>3</sub> (Ln = Nd (1), Sm (2), Eu (3), Yb (4), La (5)), combined with chiral salen ligands H<sub>2</sub>L<sup>a</sup> ((<i>S</i>,<i>S</i>)-<i>N</i>,<i>N</i>'-di-(3,5-disubstituted-salicylidene)-1,2-cyclohexanediamine) and H<sub>2</sub>L<sup>b</sup> ((<i>S</i>,<i>S</i>)-<i>N</i>,<i>N</i>'-di-(3,5-disubstituted-salicylidene)-1,2-diphenyl-1,2-ethanediamine) were employed in the enantioselective epoxidation of α,β-unsaturated  ...[more]

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