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Remote 1,5-Stereoselectivity Control by an N-Ligand Switch in the Pd(0)/InI-Promoted Reactions of 4-Ethynyl-β-lactams with Aldehydes

Author:
Domin, Sylwia, Kędzierski, Jacek, Zambroń, Bartosz K.
Source:
Organic letters 2019 v.21 no.11 pp. 3904-3908
ISSN:
1523-7052
Subject:
aldehydes, chemical structure, ligands, optical isomerism, palladium, pyridines, regioselectivity
Abstract:
Configurationally stable ε-amido-propargylindiums, generated in situ from N-Ts-4-ethynylazetidin-2-ones in the presence of InI, catalytic amounts of Pd(PPh₃)₄, and N-methylimidazole or pyridine ligand react with unusual regioselectivity with aromatic and aliphatic aldehydes to afford 2,6-syn- or 2,6-anti-allenediols with excellent central-to-axial chirality transfer and useful levels of acyclic remote 1,5-stereocontrol.
Agid:
6464080