Highly diastereoselective aziridination of α,β-unsaturated amides using diaziridine

Hiroyuki Ishihara; Yoshio N. Ito; Tsutomu Katsuki

doi:10.1246/cl.2001.984

Highly diastereoselective aziridination of α,β-unsaturated amides using diaziridine

Hiroyuki Ishihara, Yoshio N. Ito, Tsutomu Katsuki

Organic and Biological Chemistry

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

14 Citations (Scopus)

Abstract

Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with α,β-unsaturated amides in basic conditions, giving N-unprotected trans-aziridines, while 3,3-pentamethylenediaziridine had been reported to afford cis-aziridines in high diastereoselectivity. The trans-selectivity was partially dependent on the stereochemistry of the substrate. The stereochemistries of these reactions were reasonably explained by the conformational analysis of the intermediary enolates.

Original language	English
Pages (from-to)	984-985
Number of pages	2
Journal	Chemistry Letters
Issue number	10
DOIs	https://doi.org/10.1246/cl.2001.984
Publication status	Published - 2001

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.2001.984

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abstract = "Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with α,β-unsaturated amides in basic conditions, giving N-unprotected trans-aziridines, while 3,3-pentamethylenediaziridine had been reported to afford cis-aziridines in high diastereoselectivity. The trans-selectivity was partially dependent on the stereochemistry of the substrate. The stereochemistries of these reactions were reasonably explained by the conformational analysis of the intermediary enolates.",

author = "Hiroyuki Ishihara and Ito, {Yoshio N.} and Tsutomu Katsuki",

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doi = "10.1246/cl.2001.984",

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journal = "Chemistry Letters",

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AU - Ishihara, Hiroyuki

AU - Ito, Yoshio N.

AU - Katsuki, Tsutomu

PY - 2001

Y1 - 2001

N2 - Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with α,β-unsaturated amides in basic conditions, giving N-unprotected trans-aziridines, while 3,3-pentamethylenediaziridine had been reported to afford cis-aziridines in high diastereoselectivity. The trans-selectivity was partially dependent on the stereochemistry of the substrate. The stereochemistries of these reactions were reasonably explained by the conformational analysis of the intermediary enolates.

AB - Racemic 3-cyclohexyl-1-methyldiaziridine was found to react with α,β-unsaturated amides in basic conditions, giving N-unprotected trans-aziridines, while 3,3-pentamethylenediaziridine had been reported to afford cis-aziridines in high diastereoselectivity. The trans-selectivity was partially dependent on the stereochemistry of the substrate. The stereochemistries of these reactions were reasonably explained by the conformational analysis of the intermediary enolates.

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ER -

Highly diastereoselective aziridination of α,β-unsaturated amides using diaziridine

Abstract

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