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Conjugate Addition to Phenylglycinol-Derived Unsaturated ä-Lactams. Enantioselective Synthesos of Uleine Alkaloids
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The stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2indoleaceticenolatesandsulfur-stabilizedanions)tothephenylglycinol-derivedunsaturatedlactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 is studied. The factors governing the exo or endo facial stereoselectivity are discussed. This methodology provides short synthetic routes to either cis- ortrans-3,4-disubstituted enantiopure piperidines as well as efficient routes for the enantioselective construction of the tetracyclic ring system of uleine alkaloids, both in the normal and 20-epi series. The formal total synthesis of several alkaloids of this group is reported.
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AMAT TUSÓN, Mercedes, et al. Conjugate Addition to Phenylglycinol-Derived Unsaturated ä-Lactams. Enantioselective Synthesos of Uleine Alkaloids. Journal of Organic Chemistry. 2004. Vol. 69, num. 25, pags. 8681-8693. ISSN 0022-3263. [consulted: 22 of May of 2026]. Available at: https://hdl.handle.net/2445/159897