Eight-Membered and Larger Rings

Newkome, George R.; Chakraborty, Sourav

doi:10.1016/b978-0-08-102310-5.00017-5

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“…Medium-sized N-heterocyclic compounds are prevalent in biologically active natural products and pharmaceutically significant molecules, in addition to being common components of electronic devices . The cycloaddition process, which involves a direct and modular approach, is more reliable than conventional synthetic methods for constructing medium-sized N-heterocyclic compounds .…”

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confidence: 99%

Synthesis of Chiral Diazocine Derivatives via a Copper-Catalyzed Dearomative [5+3] Cycloaddition

2022

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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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confidence: 99%