4.8 Article

Ir-Catalyzed Enantioconvergent Synthesis of Diversely Protected Allenylic Amines Employing Ammonia Surrogates

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 38, Pages 16404-16408

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005599

Keywords

allenes; amination; enantioconvergent catalysis; heterocycles; iridium

Funding

  1. ETH Zurich
  2. National Sciences and Engineering Research Council of Canada

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The first iridium catalyzed, enantioconvergent amination of allenylic carbonates is reported. This process utilizes various commercially available carbamates and sulfonamides to generate allenylic amines including commonly employed protected groups (Boc, Fmoc, Cbz, Ts, Ns) in 62-82 % yield and 87-98 % ee. The products generated through this scalable procedure serve as effective linchpins for the rapid, enantiospecific synthesis of a wide range of complex structures.

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