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: kevin.w.hinkle
gsk.com
H. D. Dickson, S. C. Smith, K. W. Hinkle, Tetrahedron Lett., 2004, 45, 5597-5599.
DOI: 10.1016/j.tetlet.2004.05.139
Abstract
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
