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DOI: 10.1055/s-0035-1562445
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
Publication History
Received: 14 May 2016
Accepted after revision: 06 June 2016
Publication Date:
07 July 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201619/lookinside/thumbnails/ss-2016-c0355-op_10-1055_s-0035-1562445-1.jpg)
To the memory of Jean Normant for his contributions to organic synthesis
Abstract
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.
Key words
Suzuki reactions - cross-coupling - cyanohydrins - amino alcohols - boronic acids - palladium catalysisSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562445. Results from competition experiments, NMR spectra, HPLC, and computational details are included.
- Supporting Information
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