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Intermolecular Stereospecific Substitution of Underivatized Enantioenriched Secondary Alcohols by Organocatalysis
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8735-5397
Number of Authors: 22019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 50, p. 17908-17910Article in journal (Refereed) Published
Abstract [en]

The stereospecific substitution of non-derivatized and non-allylic enantioenriched alcohols with only water as a by-product would enable the use of readily available alcohols as substrates for green and sustainable transformations. However, the poor leaving group ability of the OH group has hampered the development of such a process. Denton and co-workers recently described the use of (2-hydroxybenzyl)diphenylphosphine oxide as a catalyst of a redox-neutral and zero-waste-generating Mitsunobu reaction. This innovative process constitutes the first intermolecular stereospecific substitution of non-allylic alcohols, and might find industrial applications.

Place, publisher, year, edition, pages
2019. Vol. 58, no 50, p. 17908-17910
Keywords [en]
alcohols, green chemistry, Mitsunobu reaction, organocatalysis, stereospecific substitution
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-176559DOI: 10.1002/anie.201911532ISI: 000494496500001PubMedID: 31693272OAI: oai:DiVA.org:su-176559DiVA, id: diva2:1379664
Available from: 2019-12-17 Created: 2019-12-17 Last updated: 2020-01-03Bibliographically approved

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