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  • Title: Diastereoselective nickel-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant: scope and mechanistic insight.
    Author: Joensuu PM, Murray GJ, Fordyce EA, Luebbers T, Lam HW.
    Journal: J Am Chem Soc; 2008 Jun 11; 130(23):7328-38. PubMed ID: 18481861.
    Abstract:
    In the presence of diethylzinc as a stoichiometric reductant, Ni(acac) 2 functions as an efficient precatalyst for the reductive aldol cyclization of alpha,beta-unsaturated carbonyl compounds tethered to a ketone electrophile through an amide or an ester linkage. The reactions are tolerant of a wide range of substitution at both alpha,beta-unsaturated carbonyl and ketone components and proceed smoothly to furnish beta-hydroxylactams and beta-hydroxylactones with generally high diastereoselectivities. A series of experiments, including deuterium-labeling studies, was carried out in an attempt to gain some insight into the possible reaction mechanisms that might be operative.
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