Synthesis, Enantiomeric Conformations, and Stereodynamics of Aromatic o rtho -Substituted Disulfones
2001; American Chemical Society; Volume: 3; Issue: 9 Linguagem: Inglês
10.1021/ol015804d
ISSN1523-7060
AutoresJérôme Lacour, David Monchaud, Gérald Bernardinelli, France Favarger,
Tópico(s)Axial and Atropisomeric Chirality Synthesis
Resumo[structure in text] Aromatic ortho-disulfone derivatives are readily accessible from diiodide precursors by Cu(I)-mediated reactions with sodium sulfinate salts. The sulfone substituents adopt C(2)-symmetric enantiomeric conformations (lambda and delta) as evidenced by X-ray structural analysis and (1)H and (31)P NMR on chiral bis(sulfonyl)veratrol derivatives and hexacoordinated tris(benzenediolato)phosphate anions. Slow dynamic conformational isomerism (DeltaG(++) > or = 19.8 kcal mol(-1)) was detected in solution.
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