Intramolecular nicholas reaction: Stereoselective synthesis of 5-alkynylproline derivatives

Organic Letters

Volumn 10, Issue 12, 2008, Pages 2349-2352

  Hernández, J Nicolás ^a   Ramírez, Miguel A ^a   Rodríguez, Matías L ^a   Martín, Víctor S ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; DRUG DERIVATIVE; PROLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; CYCLIZATION; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 48849110611     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800544a     Document Type: Article

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23. 1H NMR of the reaction mixture after workup shows virtually pure samples of the propargylic alcohols even at 0.1 M scale.
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25. When performing the reaction at -20°C, the protected N-Boc-pyrolidine is detected in the reaction mixture that gives rise to the unprotected amine.
26. Only one stereoisomer was detected by NMR analysis.
27. max = 73.9° and I > 2σ(I) criterion) and 228 parameters); maximum and minimum residues are 0.38 and 0.29, respectively. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data-request/ cif.
28. Semiempirical quantum mechanics method using a minimal valence basis set of Slater-type orbitals. Spartan'06 package, Wavefunction, Inc. (http://www.wavefun.com).