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A convenient scalable one-pot conversion of esters and Weinreb amides to terminal alkynes

Hamilton D. Dickson, Stephon C. Smith and Kevin W. Hinkle

*Microbial, Musculoskeletal, and Proliferative Diseases Medicinal Chemistry, GlaxoSmithKline, RTP, NC 27709, USA, Email:

H. D. Dickson, S. C. Smith, K. W. Hinkle, Tetrahedron Lett., 2004, 45, 5597-5599.

DOI: 10.1016/j.tetlet.2004.05.139


Esters and Weinreb amides undergo reduction to the corresponding aldehydes using DIBAL-H followed by same pot conversion to terminal alkynes utilizing the Bestmann-Ohira reagent in good to excellent yields.

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Key Words

DIBAL-H, Bestmann-Ohira Reagent, Seyferth-Gilbert Homologation, Terminal Alkynes, Weinreb Amides

ID: J72-Y2004-2500