Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines

A new asymmetric approach to assemble cis-vinyl aziridines is reported. A reaction of strategically substituted dienolates, decorated with a γ-leaving group, with chiral sulfinimines afforded chiral vinyl aziridine products in good to excellent yields. This is the first systematic study toward the r...

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Bibliographic Details
Published in:Organic letters 2018-08, Vol.20 (16), p.4942-4945
Main Authors: Chogii, Isaac, Das, Pradipta, Delost, Michael D, Crawford, Mark N, Njardarson, Jon T
Format: Article
Language:English
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Summary:A new asymmetric approach to assemble cis-vinyl aziridines is reported. A reaction of strategically substituted dienolates, decorated with a γ-leaving group, with chiral sulfinimines afforded chiral vinyl aziridine products in good to excellent yields. This is the first systematic study toward the realization of a useful asymmetric vinylogous aza-Darzens reaction. The reaction is initiated by a syn-selective addition, affording cis-vinyl aziridine products after displacement of bromide. The low syn-diastereoselectivity is attributed to competing retro-Mannich pathways.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02074