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Synthesis of Chiral Diazocine Derivatives via a Copper-Catalyzed Dearomative [5+3] Cycloaddition
Ju Young Lee1, Rohit Kumar Varshnaya1, Eun Jeong Yoo1
1Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Republic of Korea.
Abstract:
Copper-catalyzed [5+3] cycloaddition of N-aromatic zwitterions and enol diazoacetates produced enantio-enriched diazocine derivatives. A sterically encumbered BOX ligand and NaBArF additive played significant roles in driving the overall catalytic process via the unfavorable dearomatization to construct the desired eight-membered heterocyclic compounds. The induced stereoselectivity was preserved after further modifications of the skeleton, which demonstrates the potential applications of the developed asymmetric catalysis.
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