☆ 4.8 Article

Catalytic Synthesis of N-Unprotected Piperazines, Morpholines, and Thiomorpholines from Aldehydes and SnAP Reagents

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Volume 54, Issue 37, Pages 10884-10888

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.201505167

Keywords

aldehydes; cross-coupling; homogeneous catalysis; nitrogen heterocycles; SnAP reagents

Categories

Chemistry, Multidisciplinary

Funding

ETH Research Grant [ETH-12 11-1]
European Research Council (ERC) [306793]
European Research Council (ERC) [306793] Funding Source: European Research Council (ERC)

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Abstract

Commercially available SnAP (stannyl amine protocol) reagents allow the transformation of aldehydes and ketones into a variety of N-unprotected heterocycles. By identifying new ligands and reaction conditions, a robust catalytic variant that expands the substrate scope to previously inaccessible heteroaromatic substrates and new substitution patterns was realized. It also establishes the basis for a catalytic enantioselective process through the use of chiral ligands.

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