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Straightforward alpha-Amino Nitrile Synthesis Through Mo(CO)(6)-Catalyzed Reductive Functionalization of Carboxamides
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0001-5887-4630
2018 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 38, p. 12347-12351Article in journal (Refereed) Published
Abstract [en]

The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)(6) together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of alpha-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of alpha-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2018. Vol. 57, no 38, p. 12347-12351
Keywords [en]
chemoselectivity, cyanation, hydrosilylation, molybdenum, reductive functionalization
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-152250DOI: 10.1002/anie.201807735ISI: 000444225100021PubMedID: 30084524OAI: oai:DiVA.org:umu-152250DiVA, id: diva2:1253329
Funder
Knut and Alice Wallenberg FoundationSwedish Research CouncilAvailable from: 2018-10-04 Created: 2018-10-04 Last updated: 2018-10-04Bibliographically approved

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Trillo, PazAdolfsson, Hans

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