Intramolecular Nicholas Reaction: Stereoselective Synthesis of 5-Alkynylproline Derivatives

Intramolecular Nicholas Reaction: Stereoselective Synthesis of 5-Alkynylproline Derivatives

The 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 ste...

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Veröffentlicht in:Organic letters 2008-06, Vol.10 (12), p.2349-2352
Hauptverfasser: Hernández, J. Nicolás, Ramírez, Miguel A, Rodríguez, Matías L, Martín, Víctor S
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemical synthesis
Alkynes - chemistry
Cyclization
Molecular Structure
Proline - analogs & derivatives
Proline - chemical synthesis
Proline - chemistry
Stereoisomerism
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Zusammenfassung:The 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800544a