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- Title
A Regio‐ and Stereodivergent Synthesis of Homoallylic Amines by a One‐Pot Cooperative‐Catalysis‐Based Allylic Alkylation/Hofmann Rearrangement Strategy.
- Authors
Pearson, Colin M.; Fyfe, James W. B.; Snaddon, Thomas N.
- Abstract
Herein, we report a modular synthetic route to linear and branched homoallylic amines that operates through a sequential one‐pot Lewis base/transition‐metal catalyzed allylic alkylation/Hofmann rearrangement strategy. This protocol is operationally trivial, proceeds from simple and easily prepared substrates and catalysts, and enables all aspects of regio‐ and stereoselectivity to be controlled through a conserved experimental protocol. Overall, the high levels of enantio‐, regio‐, and diastereoselectivity obtained, in concert with the ability to access orthogonally protected or free amines, render this a straightforward and effective approach for the preparation of useful enantioenriched homoallylic amines. We have also demonstrated the utility of the products in the context of pharmaceutical synthesis.
- Subjects
ALLYLIC alkylation; ALLYLIC amination; AMINE synthesis; STEREOSELECTIVE reactions
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 31, p10631
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201905426