Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines

Isaac Chogii, Pradipta Das, Michael D. Delost, Mark N. Crawford, Jon T Njardarson

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)4942-4945
Number of pages4
JournalOrganic Letters
Volume20
Issue number16
DOIs
StatePublished - Aug 17 2018

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Aziridines
Bromides
products
bromides
aziridine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines. / Chogii, Isaac; Das, Pradipta; Delost, Michael D.; Crawford, Mark N.; Njardarson, Jon T.

In: Organic Letters, Vol. 20, No. 16, 17.08.2018, p. 4942-4945.

Research output: Contribution to journalArticle

Chogii, Isaac ; Das, Pradipta ; Delost, Michael D. ; Crawford, Mark N. ; Njardarson, Jon T. / Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines. In: Organic Letters. 2018 ; Vol. 20, No. 16. pp. 4942-4945.
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