A study into asymmetric Nicholas cyclisation reactions

Tetrahedron

Volumn 63, Issue 51, 2007, Pages 12769-12778

  Tyrrell, Elizabeth ^a   Millet, Julien ^a   Tesfa, Kibur Hunie ^a   Williams, Neil ^a   Mann, Alastair ^a   Tillett, Caroline ^a   Muller, Christophe ^a  

^a KINGSTON UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZOPYRAN DERIVATIVE; CITRONELLAL; SALICYLALDEHYDE;

ALKYNYLATION; ARTICLE; CYCLIZATION; NICHOLAS REACTION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; RACEMIZATION; STEREOCHEMISTRY;

EID: 35748980292     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.077     Document Type: Article

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29. 1H NMR spectroscopy from the measurement of the integrals attributed to the β-methyl groups for each of the diastereoisomers. The configuration of 10 was confirmed by its synthesis using an alternative route. This involved reacting the lithium anion of isoxazolidinone 9 with the acyl chloride derivative of (R)-citronellic acid. GC-MS analysis of this derivative showed a retention time 16.26 min and the corresponding diastereoisomer derived from(S)-citronellic acid had a retention time of 16.12 min. GC-MS analysis of compound 10, mixture of diastereisomers, showed a major peak with a retention time of 16.11 min and a minor peak with retention time of 16.25 min. With these data we were able to confirm the configuration of the major diastereoisomer of 10 as C3-(S).
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46. All compounds provided satisfactory spectral data that were consistent with the assigned structures. Optical rotation data and HPLC/GC-MS retention times are included for all relevant examples.
47. To remove faster moving and base line residues only.