Reductive cyclization and petasis-like reaction for the synthesis of functionalized γ-lactams

• Main Authors: Wu, Peng, Petersen, Michael Åxman, Cohrt, A. Emil, Petersen, Rico, Clausen, Mads H., Nielsen, Thomas E.
• Other Authors: Singapore Centre for Environmental Life Sciences Engineering
• Format: Article
• Language: English
• Published: 2015
• Subjects: DRNTU::Science::Chemistry::Organic chemistry
• Online Access: https://hdl.handle.net/10356/107135; http://hdl.handle.net/10220/25347; http://dx.doi.org/10.1002/ejoc.201500143
• Institution: Nanyang Technological University

An efficient reductive cyclization strategy was employed for the synthesis of N-substituted β,γ-dihydroxy-γ-lactams. A subsequent Petasis-like reaction (PLR) through nucleophilic additions of boronic acids to intermediate N-acyliminium ions produced substituted γ-lactams. Overall, the application of this protocol provides β,γ-dihydroxy-γ-lactams and functionalized γ-lactams with potential interest for synthetic and bioorganic chemistry.