Li + and Na + switch of enantioselectivity in the desymmetrisation of polycyclic bis(phenylsulfonyl)alkenes by chiral alcohols

A complete switch of enantioselectivity is obtained in the desymmetrisation reaction of polycyclic bis(phenylsulfonyl)alkenes by the change of the base from n-BuLi to NaH, thus allowing convenient access to either enantiomer of polycyclic ketones with the same chiral auxiliary.

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Bibliographic Details
Published in:Tetrahedron letters 2000-09, Vol.41 (37), p.7263-7266
Main Authors: Cossu, Sergio, De Lucchi, Ottorino, Peluso, Paola, Volpicelli, Raffaella
Format: Article
Language:English
Subjects:
desymmetrisation
enantiotopic discrimination
polycyclic ketones
sulfones
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Summary:A complete switch of enantioselectivity is obtained in the desymmetrisation reaction of polycyclic bis(phenylsulfonyl)alkenes by the change of the base from n-BuLi to NaH, thus allowing convenient access to either enantiomer of polycyclic ketones with the same chiral auxiliary.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)01261-2