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Sequential Formal [4+1]‐Cycloaddition, C−H Functionalization and Suzuki–Miyaura Cross‐Coupling for the Synthesis of Trisubstituted Isoxazolines
Author(s) -
Ushakov Pavel Yu.,
Sukhorukov Alexey Yu.,
Ioffe Sema L.,
Tabolin Andrey A.
Publication year - 2021
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.202100313
Subject(s) - chemistry , cycloaddition , sulfonium , surface modification , ketone , combinatorial chemistry , coupling reaction , organic chemistry , catalysis , salt (chemistry)
Suzuki–Miyaura cross‐coupling reaction of 3‐bromomethyl isoxazolines with arylboronic acids was suggested as final C−C bond forming step in convenient diastereoselective route to trisubstituted isoxazolines. The required bromides were readily available from nitroalkenes and sulfonium ylides through an efficient sequence of formal [4+1]‐cycloaddition and C−H functionalization of intermediate isoxazoline N ‐oxides. The synthetic utility of the obtained isoxazolines was demonstrated by their conversion into valuable products such as hydroxy ketone, pyrrolidinone, etc.