Stereoselective Formation of Quaternary Carbon Centers: Alkylation of α,α-Disubstituted Amide Enolates†
Jeffrey M. Manthorpe
Department of Chemistry McGill University 801 Sherbrooke St. West, Montreal, QC, H3A 2 K6 (Canada) Fax: (+1) 514-398-3797
Search for more papers by this authorJames L. Gleason Prof.
Department of Chemistry McGill University 801 Sherbrooke St. West, Montreal, QC, H3A 2 K6 (Canada) Fax: (+1) 514-398-3797
Search for more papers by this authorJeffrey M. Manthorpe
Department of Chemistry McGill University 801 Sherbrooke St. West, Montreal, QC, H3A 2 K6 (Canada) Fax: (+1) 514-398-3797
Search for more papers by this authorJames L. Gleason Prof.
Department of Chemistry McGill University 801 Sherbrooke St. West, Montreal, QC, H3A 2 K6 (Canada) Fax: (+1) 514-398-3797
Search for more papers by this authorWe thank NSERC, Research Corporation, and Merck Frosst Therapeutic Inc. for support of this research. J.M.M. acknowledges support from FCAR in the form of a postgraduate fellowship.
Graphical Abstract
Mit hoher Diastereoselektivität gelingt die Alkylierung von α,α-disubstituierten Amidenolaten zu Produkten mit quartären Kohlenstoffatomen (siehe Schema). Dabei werden weder für die Stereoselektivität der Enolatbildung noch für die der Alkylierungen chelatisierende Gruppen benötigt. Oft ist die Diastereoselektivität der Alkylierung höher als das Isomerenverhältnis der Enolat-Zwischenprodukte.
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