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DOI: 10.1055/s-2003-43373
From Allylic Alcohols to Aldols via a Novel, Efficient Reaction Catalyzed by Ni-Complexes
Publikationsverlauf
Publikationsdatum:
04. Dezember 2003 (online)
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Abstract
Allylic alcohols react with aldehydes, in an atom economic aldol-type reaction, in the presence of a catalytic amount of (dppe)NiHCl/MgBr2 mixture. This reaction occurs in good to excellent yields with total regiocontrol and very high chemo control under mild conditions. It is compatible with various types of aldehydes including very bulky ones.
Key words
allylic alcohols - double bond isomerization - aldol reaction - nickel hydrides
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References
The stereoisomeric ratios were established by 1H NMR on the crude reaction mixture. The relative stereochemistries were attributed by comparison with literature data or according to the following empirical rule: The C of the CHOH group is deshielded in the anti-adduct compared to the syn-adduct and the H of the CHOH group is shielded in the anti-adduct compared to the syn-adduct.