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

Fabian Glatz; David A Petrone; Erick M Carreira

doi:10.1002/anie.202005599

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

Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16404-16408. doi: 10.1002/anie.202005599. Epub 2020 Jul 22.

Authors

Fabian Glatz¹, David A Petrone¹, Erick M Carreira¹

Affiliation

¹ Laboratorium für Organische Chemie, HCI H335, Eidgenössiche Technische Hochschule Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.

PMID: 32558158
DOI: 10.1002/anie.202005599

Abstract

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.

Keywords: allenes; amination; enantioconvergent catalysis; heterocycles; iridium.

Publication types

Research Support, Non-U.S. Gov't