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Stereoselective Michael‐Type Addition of Organocopper Reagents to Enones Derived from Glycals in the Synthesis of 2‐Phosphono‐α‐ C ‐Glycosides
Author(s) -
Leonelli Francesca,
Capuzzi Marinella,
Calcagno Vincenzo,
Passacantilli Pietro,
Piancatelli Giovanni
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500149
Subject(s) - chemistry , enol , stereoselectivity , reagent , glycoside , michael reaction , organic chemistry , stereochemistry , catalysis
Michael‐type additions of various organocopper reagents to the novel carbohydrate‐derived 2‐(diethoxyphosphoryl)hex‐1‐en‐3‐uloses are described. The reactions have proved to be rapid, clean and stereoselective, giving rise to the formation of 3‐oxo‐2‐phosphono‐α‐ C ‐glycosides or the corresponding enol acetates. These compounds are direct precursors of 2‐phosphono‐α‐ C ‐glycosides, a very interesting class of molecules never described before. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)