Combining Two-Directional Synthesis and Tandem Reactions, Part 8: A Novel Condensation/Michael Addition/Cycloaddition/Fragmentation/Lactamisation Cascade

Sinclair, Alex, Arini, Louise, Rejzek, Martin, Szeto, Peter and Stockman, Robert (2006) Combining Two-Directional Synthesis and Tandem Reactions, Part 8: A Novel Condensation/Michael Addition/Cycloaddition/Fragmentation/Lactamisation Cascade. Synlett, 2006(14), pp. 2321-2324. ISSN (print) 0936-5214

Abstract

A tandem oxime formation/Michael addition/1,4-prototopic shift/[3+2]-cycloaddition of an acyclic symmetrical precursor results in a tricyclic isooxazolidine which then undergoes a further fragmentation/lactamisation cascade to generate a non-symmetrical tricyclic a-ketolactam as a single diastereomer

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