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Iridium‐Catalyzed Intramolecular Asymmetric Allylic Dearomatization of Benzene Derivatives
Author(s) -
Yang ZePeng,
Jiang Ru,
Wu QingFeng,
Huang Lin,
Zheng Chao,
You ShuLi
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810900
Subject(s) - chemistry , allylic rearrangement , intramolecular force , substituent , iridium , benzene , malonate , nucleophile , catalysis , reactivity (psychology) , enantioselective synthesis , ring (chemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology
Abstract Guided by the mechanistic insights from computational studies, we have developed an Ir‐catalyzed asymmetric intramolecular allylic dearomatization reaction of benzene derivatives. Under the optimized conditions consisting of a readily available Ir catalyst, a series of spiro[4.5]cyclohexadiene compounds were delivered in reasonable yields (up to 79 %) with good enantioselectivity (up to 99 % ee ). The introduction of a malonate diester‐type substituent serves as a key strategy to guide the nucleophilic reactivity of the benzene ring.