Tetrahedron p. 2841 - 2848 (1994)
Update date:2022-08-05
Topics:
Szymoniak, Jan
Besancon, Jack
Moise, Claude
NbCl3 (DME) was found to be a useful reagent for the intermolecular pinacol coupling of aliphatic aldehydes.The high anti diastereoselectivity of this reaction (dl / meso >/= 9 / 1) did not depend on the variation in the aldehyde alkyl chain.With respect to intramolecular pinacolization, the loss of the stereoselectivity observed is consistent with the mechanism involving an insertion of the oxo-group into the metal-carbon bond of the intermediate niobiooxirane. - Key Words: Nb(III) reagent; Pinacol coupling; Acetalization; Stereoselectivity
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