Palladium(II) Acetate Catalyzed Stereoselective C-Glycosidation of Peracetylated Glycals with Arylboronic Acids

Palladium(II) Acetate Catalyzed Stereoselective C-Glycosidation of Peracetylated Glycals with Arylboronic Acids

Addition of a variety of arylboronic acids to peracetylated glycals takes place in the presence of a catalytic amount of Pd(OAc)2. The reaction involves the syn addition of a σ-aryl-Pd complex to the glycal double bond followed by anti elimination of Pd(OAc)2 to provide a carbon-Ferrier type product...

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Veröffentlicht in:Organic letters 2001-06, Vol.3 (13), p.2013-2015
Hauptverfasser: Ramnauth, Jailall, Poulin, Odile, Rakhit, Suman, Maddaford, Shawn P
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container_issue 13
container_start_page 2013
container_title Organic letters
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creator Ramnauth, Jailall
Poulin, Odile
Rakhit, Suman
Maddaford, Shawn P
description Addition of a variety of arylboronic acids to peracetylated glycals takes place in the presence of a catalytic amount of Pd(OAc)2. The reaction involves the syn addition of a σ-aryl-Pd complex to the glycal double bond followed by anti elimination of Pd(OAc)2 to provide a carbon-Ferrier type product. This method provides a practical and convenient stereoselective synthesis of C-arylglycosides.
doi_str_mv 10.1021/ol010070q
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title Palladium(II) Acetate Catalyzed Stereoselective C-Glycosidation of Peracetylated Glycals with Arylboronic Acids
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