Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination
A Kallinen, J Tois, R Sjöholm, R Franzén
Index: Kallinen, Annukka; Tois, Jan; Sjoeholm, Rainer; Franzen, Robert Tetrahedron Asymmetry, 2010 , vol. 21, # 19 p. 2367 - 2371
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Citation Number: 7
Abstract
Stereoselective synthesis of (5R, 6R)-and (5S, 6S)-5-benzylamino-6-(tert- butyldimethylsilanyloxymethyl)-5, 6-dihydropyran-2-ones starting from d-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps.
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