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Intramolecular Umpolung Synthesis of Exocyclic β‑Amino Alcohols through Decarboxylative Amination

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https://figshare.com/articles/dataset/Intramolecular_Umpolung_Synthesis_of_Exocyclic_Amino_Alcohols_through_Decarboxylative_Amination/7289285
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An intramolecular aminative Umpolung cyclization strategy has been developed by using α,α-diphenylglycine (2) as the amination and Umpolung reagent. Aldehydes (1) bearing an additional carbonyl group underwent condensation with α,α-diphenylglycine to form an imine, decarboxylation to generate a delocalized 2-azaallylanion, and subsequent intramolecular Umpolung cyclization to produce a variety of exocyclic β-amino alcohols (6) in 60–93% yields with up to >20:1 trans/cis selectivity under mild conditions.
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2018-11-01
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