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Construction of Isoxazolidines through Formal [3+2] Cycloaddition Reactions of in situ Generated Nitrosocarbonyls with Donor–Acceptor Cyclopropanes: Synthesis of α‐Amino γ‐Butyrolactones
Author(s) -
Varshnaya Rohit Kumar,
Banerjee Prabal
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600582
Subject(s) - chemistry , cycloaddition , in situ , cleavage (geology) , acceptor , stereochemistry , catalysis , combinatorial chemistry , bond cleavage , organic chemistry , physics , geotechnical engineering , fracture (geology) , engineering , condensed matter physics
A straightforward approach for the synthesis of isoxazolidines through MgI 2 ‐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.