DMF as a source of oxygen and aminomethine: Stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes into the C=O bond of formamides for the synthesis of cis -diamino enones

Da Jung Jung; Hyun Ji Jeon; Ju Hyun Kim; Youngmee Kim; Sang Gi Lee

doi:10.1021/ol500723s

DMF as a source of oxygen and aminomethine: Stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes into the C=O bond of formamides for the synthesis of cis -diamino enones

Da Jung Jung, Hyun Ji Jeon, Ju Hyun Kim, Youngmee Kim, Sang Gi Lee

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

80 Scopus citations

Abstract

A new catalytic reaction in which all the atoms of a formamide are incorporated into the product through a formal stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes, generated in situ from readily available N-sulfonylated 1,2,3-triazoles, into the C=O bond of DMF and other N,N-disubstituted formamides to afford cis-diamino enones is described.

Original language	English
Pages (from-to)	2208-2211
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	8
DOIs	https://doi.org/10.1021/ol500723s
State	Published - 18 Apr 2014

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abstract = "A new catalytic reaction in which all the atoms of a formamide are incorporated into the product through a formal stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes, generated in situ from readily available N-sulfonylated 1,2,3-triazoles, into the C=O bond of DMF and other N,N-disubstituted formamides to afford cis-diamino enones is described.",

author = "Jung, {Da Jung} and Jeon, {Hyun Ji} and Kim, {Ju Hyun} and Youngmee Kim and Lee, {Sang Gi}",

year = "2014",

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T1 - DMF as a source of oxygen and aminomethine

T2 - Stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes into the C=O bond of formamides for the synthesis of cis -diamino enones

AU - Jung, Da Jung

AU - Jeon, Hyun Ji

AU - Kim, Ju Hyun

AU - Kim, Youngmee

AU - Lee, Sang Gi

PY - 2014/4/18

Y1 - 2014/4/18

N2 - A new catalytic reaction in which all the atoms of a formamide are incorporated into the product through a formal stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes, generated in situ from readily available N-sulfonylated 1,2,3-triazoles, into the C=O bond of DMF and other N,N-disubstituted formamides to afford cis-diamino enones is described.

AB - A new catalytic reaction in which all the atoms of a formamide are incorporated into the product through a formal stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes, generated in situ from readily available N-sulfonylated 1,2,3-triazoles, into the C=O bond of DMF and other N,N-disubstituted formamides to afford cis-diamino enones is described.

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DO - 10.1021/ol500723s

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DMF as a source of oxygen and aminomethine: Stereoselective 1,2-insertion of rhodium(II) azavinyl carbenes into the C=O bond of formamides for the synthesis of cis -diamino enones

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