Reductive Cyclization and Petasis‐Like Reaction for the Synthesis of Functionalized γ‐Lactams. Issue 11 (9th March 2015)

• Record Type: Journal Article
• Authors: Wu, Peng; Petersen, Michael Åxman; Cohrt, A. Emil; Petersen, Rico; Clausen, Mads H.; Nielsen, Thomas E.
• Is Part Of: European journal of organic chemistry. Issue 11(2015)
• Page Start: 2346
• Page End: 2350
• Publication Date: 2015-03-09
• Subjects: Reductive cyclization -- Petasis‐like reaction -- Lactams -- Nucleophilic addition -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500143
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : A novel approach to N ‐substituted β, γ‐dihydroxy‐γ‐lactams through reductive cyclization and a Lewis acid mediated Petasis‐like reaction to functionalized γ‐lactams through nucleophilic addition of both electron‐rich and electron‐deficient boronic acids to N ‐acyliminium ions are disclosed.