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Copper‐Catalyzed Cope‐Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development
Author(s) -
Zhang Mengru,
Liu Shuang,
Li Hexin,
Guo Yajing,
Li Na,
Guan Meihui,
Mehfooz Haroon,
Zhao Jinbo,
Zhang Qian
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902683
Subject(s) - hydroamination , catalysis , enantioselective synthesis , chemistry , combinatorial chemistry , copper , organic chemistry
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper‐catalyzed Cope‐type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five‐ and six‐membered cyclic nitrones under mild conditions. In this study, heterocycle‐tethered oximes were employed in the Cope‐type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon‐tethered γ,δ‐vinyl oximes to afford enantioenriched five‐membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.