3238-60-6Relevant articles and documents
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Just et al.
, p. 287,289,290 (1976)
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Leete
, p. 3523 (1963)
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Proline catalyzed, one-pot three component Mannich reaction and sequential cyclization toward the synthesis of 2-substituted piperidine and pyrrolidine alkaloids
Chacko, Shibin,Ramapanicker, Ramesh
supporting information, p. 2023 - 2026 (2015/03/18)
Abstract A very effective one-pot three component reaction of 4-bromobutanal or 5-bromopentanal, acetone, and p-anisidine catalyzed by proline is reported. A three component Mannich reaction followed by cyclization leading to the synthesis of 2-substituted pyrrolidine and piperidine derivatives through simultaneous formation of two C-N and one C-C bond is reported. The usefulness of the reaction is demonstrated by the synthesis of (±)coniine, (±)pelletrine, (±)sedridine, and (±)allosedridine.
Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products
Dion, Isabelle,Vincent-Rocan, Jean-Francois,Zhang, Lei,Cebrowski, Pamela H.,Lebrun, Marie-Eve,Pfeiffer, Jennifer Y.,Bedard, Anne-Catherine,Beauchemin, Andre M.
, p. 12735 - 12749 (2014/01/17)
Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.
