Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 11, Issue 13, Pages 4019-4023Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200500158
Keywords
chiral aggregates; lithium; NMR spectroscopy; structure elucidation; X-ray diffraction
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Phenyl fenchol forms a 3:1 aggregate with n-butyllithium (3-BuLi), showing unique lithium-HC agostic interactions both in toluene solution (H-1,Li-7-HOESY) and in the solid state (X-ray analysis). Although methoxy-lithium coor-dination is characteristic for many mixed aggregates of anisyl fencholates with n-butyllithium, endo-methyl coordination to lithium ions compensates for the missing methoxy groups in 3-BuLi. This gives rise to a different orientation of the fenchane moiety, encapsulating and chirally modifying the butylide unit.
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