Construction of Isoxazolidines through Formal [3+2] Cycloaddition Reactions of in situ Generated Nitrosocarbonyls with Donor–Acceptor Cyclopropanes: Synthesis of α‐Amino γ‐Butyrolactones. Issue 23 (21st July 2016)

• Record Type: Journal Article
• Authors: Varshnaya, Rohit Kumar; Banerjee, Prabal
• Is Part Of: European journal of organic chemistry. Issue 23(2016)
• Page Start: 4059
• Page End: 4066
• Publication Date: 2016-07-21
• Subjects: Synthetic methods -- Nitrogen heterocycles -- Cycloaddition -- Lewis acids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600582
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A straightforward approach for the synthesis of isoxazolidines through MgI2 ‐catalyzed [3+2] cycloaddition reactions of donor–acceptor cyclopropanes with in situ generated nitrosocarbonyls from hydroxycarbamates is described. This method facilitates one‐pot synthesis of α‐amino‐γ‐butyrolactone by deprotection, reductive cleavage of N–O bond, and successive lactonization. Abstract : MgI2 ‐catalyzed [3+2] cycloaddition reactions of donor–acceptor cyclopropanes with in situ generated nitrosocarbonyls from hydroxycarbamates is explored for the synthesis of functionalized isoxazolidines. Furthermore, isoxazolidines readily transformed into synthetically important α‐amino‐γ‐butyrolactones.