Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles

• Main Authors: Dai, Xi-Jie (Author), Engl, Oliver D. (Author), Leon Serrano, Thierry (Author), Buchwald, Stephen Leffler (Author)
• Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
• Format: Article
• Language: English
• Published: Wiley, 2020-05-19T13:09:23Z.
• Subjects: Article
• Online Access: Get fulltext

Herein, we report a practical two-step synthetic route to α-arylpyrrolidines through Suzuki-Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium-ring dibenzo-fused nitrogen heterocycles.
National Institutes of Health (U.S.) (Award R35-GM122483)
National Institutes of Health (U.S.) (Grant R01-GM058160-17S1)
Swiss National Science Foundation (Postdoctoral Fellowship P2EZP2_175140)