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Synfacts 2011(8): 0860-0860  
DOI: 10.1055/s-0030-1260747
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Propargylic Amination of Nonaromatic Propargylic Esters

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
A. Yoshida, G. Hattori, Y. Miyake, Y. Nishibayashi*
The University of Tokyo, Japan
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Publikationsdatum:
20. Juli 2011 (online)

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Significance

This paper expands the scope of suitable substrates for the enantioselective substitution onto propargyl alcohol derivatives bearing an alkyl group (cyclic or acyclic) at the propargylic position; this was achieved by replacing the common acetate leaving group by pentafluorobenzo­ate. A number of products were obtained with moderate yields (40-60%) and high enantioselectivities (77-90% ee).