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Highly Enantioselective Synthesis of Fused Tri- and Tetra-substituted Aziridines via Bifunctional Phosphonium Salt-Catalyzed Aza-Darzens Reaction.

08:00 EDT 8th April 2019 | BioPortfolio

Summary of "Highly Enantioselective Synthesis of Fused Tri- and Tetra-substituted Aziridines via Bifunctional Phosphonium Salt-Catalyzed Aza-Darzens Reaction."

The first enantioselective aza-Darzens reaction of cyclic imines with α-halogenated ketones was realized under mild reaction conditions, by using amino acid-derived bifunctional phosphonium salts as phase-transfer promoters. A variety of structurally dense tri- and tetra-substituted aziridine derivatives, containing benzo-fused heterocycles as well as spiro structures, were readily synthesized in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99.9% ee). The highly functionalized aziridine products could be easily transformed into different classes of biologically acitve compounds with signicficant synthetic challenge.

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This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
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