Enantioselective Gold(I)-Catalyzed Hydrative Cyclizations of N-Propargyl-ynamides into 3,6-Dihydropyridinones | Zendy

Julie Febvay | Zendy; Youssouf Sanogo | Zendy; Pascal Retailleau | Zendy; Manash Protim Gogoi | Zendy; Akhila K. Sahoo | Zendy; Angéla Marinetti | Zendy; Arnaud Voituriez | Zendy

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Enantioselective Gold(I)-Catalyzed Hydrative Cyclizations of N-Propargyl-ynamides into 3,6-Dihydropyridinones

Author(s) -

Julie Febvay,

Youssouf Sanogo,

Pascal Retailleau,

Manash Protim Gogoi,

Akhila K. Sahoo,

Angéla Marinetti,

Arnaud Voituriez

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b02644

Subject(s) - chemistry , propargyl , enantioselective synthesis , catalysis , diphosphines , enantiomer , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry

This study discloses the first enantioselective variant of the gold(I)-catalyzed hydrative cyclizations of ynamides, which have been implemented by using bis-gold(I) complexes of chiral diphosphines. Starting from N -propargyl-ynamides and water in the presence of p -toluenesulfonic acid, the cyclization reactions afford N -tosyl-3,6-dihydropyridin-2(1 H )-ones in good isolated yields and with high levels of stereocontrol (20 examples, enantiomeric ratios up to 94:6).

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