Diastereoselective nickel-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant: scope and mechanistic insight |
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Authors: | Joensuu Pekka M Murray Gordon J Fordyce Euan A F Luebbers Thomas Lam Hon Wai |
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Institution: | School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom. |
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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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