Regio-selective reduction of the C–C double bonds in α,β-unsaturated acyl 4-substituted oxazolidin-2-ones and oxazolidine-2-thiones

Selective saturation of the conjugated C–C double bonds in the title compounds was examined in a systematic way for the first time. Many established protocols effective for similar reduction of α,β-unsaturated ketones and esters in the literature were found to be inapplicable in the present context....

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Bibliographic Details
Published in:Tetrahedron 2012-01, Vol.68 (3), p.846-850
Main Authors: Li, Shao-Gang, Jin, Jian-Wei, Wu, Yikang
Format: Article
Language:English
Subjects:
Alkenes
Chemistry
Chiral auxiliary
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Hydride
Organic chemistry
Preparations and properties
Reduction
Stereochemistry
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Summary:Selective saturation of the conjugated C–C double bonds in the title compounds was examined in a systematic way for the first time. Many established protocols effective for similar reduction of α,β-unsaturated ketones and esters in the literature were found to be inapplicable in the present context. The most satisfactory results were finally obtained using the DIBAL-H/MeLi/CuI/HMPA/THF conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.11.038