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Synfacts 2011(6): 0634-0634  
DOI: 10.1055/s-0030-1260398
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Vinylogous Mannich Reactions of Fluorinated Aldimines and Siloxyfurans

Contributor(s): Mark Lautens, Hasnain A. Malik
Q.-Y. Zhao, Z.-L. Yuan, M. Shi*
East China University of Science and Technology, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
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Publikationsdatum:
19. Mai 2011 (online)

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Significance

The authors report a silver(I)-mediated diastereoselective synthesis of γ-butenolide and γ-lactone products. Chiral phosphine-oxazole ligands were found to provide high diastereoselectivities for a variety of fluorinated aldimines. The products were found to be amenable to reduction and/or further derivatization.