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• W2034767180 abstract "Abstract A divergent synthetic approach for the synthesis of optically pure bis(thioglycosides) of type I is reported. A common chiral intermediate with up to eight free hydroxy groups is obtained in only two steps, and from this common intermediate a large number of ligands can be synthesized. A strategy resembling positional scanning enabled the rapid discovery of an efficient catalyst for the palladium‐catalyzed asymmetric allylation of malonate. Both enantiomers of the allylated product could be obtained in up to 90 % ee values through the use of natural D ‐sugars as catalyst precursors, thanks to the structural similarity of α‐ D ‐arabinose and β‐ L ‐galactose. Treatment of several C 2 ‐symmetric bis(thioglycosides) with [PdCl 2 (CH 3 CN) 2 ] always resulted in single diastereomeric Pd II complexes. Dynamic NMR studies of various Pd II complexes have shown that there is efficient stereochemical control over the sulfur configuration upon coordination to the palladium, as a consequence of the exo ‐anomeric effect. An explanatory model for the observed enantioselectivity based on NMR studies is discussed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)" @default.
• W2034767180 created "2016-06-24" @default.
• W2034767180 creator A5028032700 @default.
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• W2034767180 date "2006-03-14" @default.
• W2034767180 modified "2023-10-18" @default.
• W2034767180 title "Sulfur–Sulfur‐Based Ligands Derived from <scp>D</scp>‐Sugars: Synthesis of Pd^II Complexes, Application in Palladium‐Catalyzed Allylic Alkylation for the Synthesis of Both Members of Enantiomer Pairs, and Structural Studies" @default.
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• W2034767180 doi "https://doi.org/10.1002/ejoc.200500651" @default.
• W2034767180 hasPublicationYear "2006" @default.
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