Intramolecular Nicholas Reaction: Stereoselective Synthesis of 5-Alkynylproline Derivatives
2008; American Chemical Society; Volume: 10; Issue: 12 Linguagem: Inglês
10.1021/ol800544a
ISSN1523-7060
AutoresJ. Nicolás Hernández, Miguel Á. Ramírez, M.L. Rodríguez, Victor S. Martı́n,
Tópico(s)Catalytic Alkyne Reactions
ResumoThe intramolecular Nicholas reaction of propargylic alcohols derived from N,N-acyl-diprotected ω-semialdehydes obtained from glutamic acid provided stereoselectively 5-alkynylproline derivatives. The suitable choice of the N-protecting group (tosyl or benzoyl derivative) permitted control of the stereochemistry during the ring formation. Semiempirical calculations of the species involved in the cyclization support the observed stereochemistry.
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