Enantioselective Reduction of Ketones Catalyzed by Rare-Earth Metals Complexed with Phenoxy Modified Chiral Prolinols

Enantioselective reduction of ketones and α,β-unsaturated ketones by pinacolborane (HBpin) has been well-established by using chiral rare-earth metal catalysts with phenoxy modified prolinols. A number of highly optically active alcohols were obtained from reduction of simple ketones catalyzed by yt...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-06, Vol.83 (11), p.6093-6100
Main Authors: Song, Peng, Lu, Chengrong, Fei, Zenghui, Zhao, Bei, Yao, Yingming
Format: Article
Language:English
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Summary:Enantioselective reduction of ketones and α,β-unsaturated ketones by pinacolborane (HBpin) has been well-established by using chiral rare-earth metal catalysts with phenoxy modified prolinols. A number of highly optically active alcohols were obtained from reduction of simple ketones catalyzed by ytterbium complex 1 [L4Yb­(L4H)] (H2L4 = (S)-2- tert-butyl-6-((2-(hydroxydiphenylmethyl)­pyrrolidin-1-yl)­methyl)­phenol). Moreover, α,β-unsaturated ketones were selectively reduced to a wide range of chiral allylic alcohols with excellent yields, high enantioselectivity, and complete chemoselectivity, catalyzed by a single component chiral ytterbium complex 2 [L1Yb­(L1H)] (H2L1 = (S)-2,4-di-tert-butyl-6-((2-(hydroxydiphenylmethyl)­pyrrolidin-1-yl)­methyl)­phenol).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00783