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Palladium-Catalyzed C(sp3)–C(sp2) Cross-Couplings of O-(α-Bromoacyl) Cyanohydrins with Boronic Acids: An Entry to Enantio­enriched N-Acylated β-Amino Alcohols
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry. Division of Organic Chemistry . (Dinér)ORCID iD: 0000-0001-6782-6622
KTH, School of Chemical Science and Engineering (CHE), Chemistry.ORCID iD: 0000-0002-1743-7650
2016 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 48, no 19Article in journal (Refereed) Published
Abstract [en]

Suzuki-type cross-coupling of enantiomerically enriched O-(α-bromoacyl) cyanohydrins with aromatic boronic acids substituted with electron-withdrawing or electron-donating groups gave the expected coupling products in high yields without racemization. These substrates exhibit higher reactivities than analogous substrates lacking the nitrile function, probably as a result of π-coordination of the nitrile to palladium. Reduction of the nitrile group of the products, with accompanying intramolecular acyl transfer, provides access to biologically interesting N-acylated β-amino alcohols.

Place, publisher, year, edition, pages
2016. Vol. 48, no 19
Keyword [en]
amino alcohols; boronic acids; cross-coupling; cyanohydrins; palladium catalysis; Suzuki reactions
National Category
Natural Sciences Organic Chemistry
Research subject
Chemistry; Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-194100DOI: 10.1055/s-0035-1562445Scopus ID: 2-s2.0-84978080539OAI: oai:DiVA.org:kth-194100DiVA: diva2:1037431
Note

QC 20161017

Available from: 2016-10-14 Created: 2016-10-14 Last updated: 2017-11-29Bibliographically approved

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