Synthesis 2016; 48(19): 3175-3182
DOI: 10.1055/s-0035-1562445
paper
© Georg Thieme Verlag Stuttgart · New York

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

Robin Hertzberg
KTH Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Teknikringen 30, 10044 Stockholm, Sweden   Email: kimo@kth.se
,
Peter Dinér
KTH Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Teknikringen 30, 10044 Stockholm, Sweden   Email: kimo@kth.se
,
Christina Moberg*
KTH Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Teknikringen 30, 10044 Stockholm, Sweden   Email: kimo@kth.se
› Author Affiliations
Further Information

Publication History

Received: 14 May 2016

Accepted after revision: 06 June 2016

Publication Date:
07 July 2016 (online)

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.

Supporting Information

 
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