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Rhodium(III)‐Catalyzed Synthesis of N ‐(2‐Acetoxyalkyl)isoquinolones from Oxazolines and Alkynes through C−N Bond Formation and Ring‐Opening
Author(s) -
Yang Zi,
Jie Lianghua,
Yao Zhenyu,
Yang Zhimin,
Cui Xiuling
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801217
Subject(s) - chemistry , rhodium , regioselectivity , catalysis , ring (chemistry) , medicinal chemistry , nucleophile , chirality (physics) , stereochemistry , nucleophilic addition , reaction mechanism , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
An atom‐economic approach for the synthesis of N ‐(2‐acetoxyalkyl)isoquinolones from oxazolines and alkynes through rhodium(III)‐catalyzed auto‐tandem reactions involving C−H bond functionalization/C−N bond formation/ring opening/nucleophilic substitution is described. This protocol features high regioselectivity, tolerance of various functional groups, and retention of absolute configuration of chirality. Exploration of the reaction mechanism reveals that Cu(OAc) 2 not only acts as the oxidant, but also provides acetate to promote the reaction in this process.