Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines

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

doi:10.1021/acs.orglett.8b02074

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 journal › Article › peer-review

8 Scopus citations

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 language	English (US)
Pages (from-to)	4942-4945
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.8b02074
State	Published - Aug 17 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b02074

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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.",

author = "Isaac Chogii and Pradipta Das and Delost, {Michael D.} and Crawford, {Mark N.} and Njardarson, {Jon T.}",

note = "Funding Information: Financial support was provided by the Foundation (CHE-1565500 to J.T.N.). Funding Information: Financial support was provided by the National Science Foundation (CHE-1565500 to J.T.N.). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Chogii, Isaac

AU - Das, Pradipta

AU - Delost, Michael D.

AU - Crawford, Mark N.

AU - Njardarson, Jon T.

N1 - Funding Information: Financial support was provided by the Foundation (CHE-1565500 to J.T.N.). Funding Information: Financial support was provided by the National Science Foundation (CHE-1565500 to J.T.N.). Publisher Copyright: © 2018 American Chemical Society.

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N2 - 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.

AB - 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.

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Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines

Abstract

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