One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the n-tosyl imine of chloroacetaldehyde with an asymmetric mannich reaction as a key step

Yujiro Hayashi; Tatsuya Urushima; Daisuke Sakamoto; Kou Torii; Hayato Ishikawa

doi:10.1002/chem.201101668

One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the n-tosyl imine of chloroacetaldehyde with an asymmetric mannich reaction as a key step

Yujiro Hayashi, Tatsuya Urushima, Daisuke Sakamoto, Kou Torii, Hayato Ishikawa

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

20 Citations (Scopus)

Abstract

Aziridines with ease: A one-pot synthesis of chiral aziridine derivatives with excellent diastereo- and enantioselectivities was developed through uninterrupted sequential reactions, including desulfonylative formation of the N-Ts imine derived from chloroacetaldehyde, a diarylprolinol silyl ether mediated asymmetric Mannich reaction, reduction, and aziridine formation (see scheme; Ts=tosyl).

Original language	English
Pages (from-to)	11715-11718
Number of pages	4
Journal	Chemistry - A European Journal
Volume	17
Issue number	42
DOIs	https://doi.org/10.1002/chem.201101668
Publication status	Published - 2011 Oct 10
Externally published	Yes

Keywords

Mannich reaction
asymmetric reaction
domino reactions
enantioselectivity
one-pot reaction
organocatalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201101668

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One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the n-tosyl imine of chloroacetaldehyde with an asymmetric mannich reaction as a key step. / Hayashi, Yujiro; Urushima, Tatsuya; Sakamoto, Daisuke et al.
In: Chemistry - A European Journal, Vol. 17, No. 42, 10.10.2011, p. 11715-11718.

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

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abstract = "Aziridines with ease: A one-pot synthesis of chiral aziridine derivatives with excellent diastereo- and enantioselectivities was developed through uninterrupted sequential reactions, including desulfonylative formation of the N-Ts imine derived from chloroacetaldehyde, a diarylprolinol silyl ether mediated asymmetric Mannich reaction, reduction, and aziridine formation (see scheme; Ts=tosyl).",

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AU - Urushima, Tatsuya

AU - Sakamoto, Daisuke

AU - Torii, Kou

AU - Ishikawa, Hayato

PY - 2011/10/10

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AB - Aziridines with ease: A one-pot synthesis of chiral aziridine derivatives with excellent diastereo- and enantioselectivities was developed through uninterrupted sequential reactions, including desulfonylative formation of the N-Ts imine derived from chloroacetaldehyde, a diarylprolinol silyl ether mediated asymmetric Mannich reaction, reduction, and aziridine formation (see scheme; Ts=tosyl).

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KW - enantioselectivity

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KW - organocatalysis

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One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the n-tosyl imine of chloroacetaldehyde with an asymmetric mannich reaction as a key step

Abstract

Keywords

ASJC Scopus subject areas

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