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Tandem Peterson olefination and chemoselective asymmetric hydrogenation of -hydroxy silanes
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 62019 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 10, no 12, p. 3649-3653Article in journal (Refereed) Published
Abstract [en]

Here, we report the first Ir-N,P complex catalyzed tandem Peterson olefination and asymmetric hydrogenation of -hydroxy silanes. This reaction resulted in the formation of chiral alkanes in high isolated yields (up to 99%) and excellent enantioselectivity (up to 99% ee) under mild conditions. Modification of the reaction conditions provides a choice to transform either an olefin or the -hydroxy silane in a chemoselective manner. Additionally, based on this method, an expedient enantioselective synthesis of (S)-(+)--curcumene, from a simple ketone, was accomplished in two steps with 75% overall yield and 95% ee.

Place, publisher, year, edition, pages
2019. Vol. 10, no 12, p. 3649-3653
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-168610DOI: 10.1039/c8sc05261aISI: 000463759100023PubMedID: 30996960OAI: oai:DiVA.org:su-168610DiVA, id: diva2:1315259
Available from: 2019-05-13 Created: 2019-05-13 Last updated: 2019-12-04Bibliographically approved

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