Stereoselective Reduction of β-Hydroxy Ketones with Aldehydes via Tishchenko Reactions Catalyzed by Zirconocene Complexes1
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ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTStereoselective Reduction of β-Hydroxy Ketones with Aldehydes via Tishchenko Reactions Catalyzed by Zirconocene Complexes1Yuuji Umekawa, Satoshi Sakaguchi, Yutaka Nishiyama, and Yasutaka IshiiView Author Information Department of Applied Chemistry, Faculty of Engineering & High Technology Research Center, Kansai University, Suita, Osaka 564, JapanCite this: J. Org. Chem. 1997, 62, 10, 3409–3412Publication Date (Web):May 16, 1997Publication History Received3 January 1997Published online16 May 1997Published inissue 1 May 1997https://pubs.acs.org/doi/10.1021/jo970031lhttps://doi.org/10.1021/jo970031lbrief-reportACS PublicationsCopyright © 1997 American Chemical SocietyRequest reuse permissionsArticle Views777Altmetric-Citations32LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Aldehydes,Ketones,Sandwich compounds,Stereoselectivity,Transfer reactions Get e-AlertsProducts with 2′-5′-linkages and Rp configurations result from the stereoselective UO-catalyzed oligomerization of the adenosine derivative 1, although the starting monomer was used as a mixture of diastereomers. The high regio-and stereoselectivity observed here is rarely encountered except in enzymatic reactions.
Diastereomer
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Abstract The cycloanellation reaction is first studied for some model compounds and thereupon used as starting step in the synthesis of the title compound (VII).
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Allyltitanocene complexes can be generated by reacting pentafulvenes with DIBAL-H and Cp2TiCl2. Their coupling with aldehydes affords homoallylic alcohols in a highly regio- and stereoselective manner. The potential of this method for the stereoselective synthesis of cyclopentane derivatives is illustrated.
Cyclopentanes
Surface Modification
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Stereoselective synthesis of 2'-C-methyl-cyclopropyl-fused carbanucleosides was accomplished via stereoselective cyclopropanation, regioselective cleavage of the isopropylidene group, stereoselective Grignard reaction, and cyclic sulfate chemistry.
Cleavage (geology)
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A remarkably stereoselective reduction of a γ-hydroxyketone with two equiv. of lithium triethylborohydride has been observed and this effect has been suggested to originate from 'chelation control'; the reaction has been utilised in a short stereoselective synthesis of ancistrofuran.
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ALUMINUM HYDRIDE
Diastereomer
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Abstract In the presence of a catalytic amount of several trityl salts, 2,3,5-tri-O-benzyl-d-ribofuranose smoothly reacted with alcohols to give various β-ribofuranosides in high yields with high stereoselectivity while reversed stereoselectivity was observed in the coexistence of lithium perchlolate.
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