Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis
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- Steven M. Banik
- Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
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- Anna Levina
- Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
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- Alan M. Hyde
- Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
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- Eric N. Jacobsen
- Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
書誌事項
- 公開日
- 2017-11-10
- DOI
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- 10.1126/science.aao5894
- 公開者
- American Association for the Advancement of Science (AAAS)
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説明
<jats:title>Lewis acid catalysis tackled by tag team</jats:title> <jats:p> Molecular catalysts with two closely spaced nitrogen-hydrogen groups can act like a tweezer, activating a carbon center by latching onto a leaving group through double hydrogen bonding and then pulling it away. In the resultant ion pair, the shape of the catalyst can bias an ensuing reaction to favor just one of two possible mirror-image products. Banik <jats:italic>et al.</jats:italic> used this motif to activate a Lewis acid cocatalyst, pulling a leaving group off silicon instead of carbon (see the Perspective by Mattson). The combined pair of catalysts is more effective for reactions such as asymmetric cycloadditions that involve weaker leaving groups on carbon. </jats:p> <jats:p> <jats:italic>Science</jats:italic> , this issue p. <jats:related-article xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="doi" issue="6364" page="761" related-article-type="in-this-issue" vol="358" xlink:href="10.1126/science.aao5894">761</jats:related-article> ; see also p. <jats:related-article xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="doi" issue="6364" page="720" related-article-type="in-this-issue" vol="358" xlink:href="10.1126/science.aaq0680">720</jats:related-article> </jats:p>
収録刊行物
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- Science
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Science 358 (6364), 761-764, 2017-11-10
American Association for the Advancement of Science (AAAS)