The practical preparation of chiral N-sulfonyl oxaziridines via catalytic asymmetric payne oxidation

Ryosuke Tsutsumi; Seonwoo Kim; Daisuke Uraguchi; Takashi Ooi

doi:10.1055/s-0033-1340818

The practical preparation of chiral N-sulfonyl oxaziridines via catalytic asymmetric payne oxidation

Ryosuke Tsutsumi, Seonwoo Kim, Daisuke Uraguchi, Takashi Ooi

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

5 Citations (Scopus)

Abstract

The asymmetric Payne oxidation of N-sulfonyl imines catalyzed by a P-spiro chiral triaminoiminophosphorane was developed for the practical synthesis of optically active N-sulfonyl oxaziridines. High efficiency and an excellent level of enantioselectivity were generally achieved with a wide variety of aldimines by choosing appropriate reaction conditions. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.

Original language	English
Article number	5440
Pages (from-to)	871-878
Number of pages	8
Journal	Synthesis (Germany)
Volume	46
Issue number	7
DOIs	https://doi.org/10.1055/s-0033-1340818
Publication status	Published - 2014 Apr
Externally published	Yes

Keywords

asymmetric catalysis
oxaziridines
oxidation
peroxides
stereoselective synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0033-1340818

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title = "The practical preparation of chiral N-sulfonyl oxaziridines via catalytic asymmetric payne oxidation",

abstract = "The asymmetric Payne oxidation of N-sulfonyl imines catalyzed by a P-spiro chiral triaminoiminophosphorane was developed for the practical synthesis of optically active N-sulfonyl oxaziridines. High efficiency and an excellent level of enantioselectivity were generally achieved with a wide variety of aldimines by choosing appropriate reaction conditions. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.",

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AU - Tsutsumi, Ryosuke

AU - Kim, Seonwoo

AU - Uraguchi, Daisuke

AU - Ooi, Takashi

PY - 2014/4

Y1 - 2014/4

N2 - The asymmetric Payne oxidation of N-sulfonyl imines catalyzed by a P-spiro chiral triaminoiminophosphorane was developed for the practical synthesis of optically active N-sulfonyl oxaziridines. High efficiency and an excellent level of enantioselectivity were generally achieved with a wide variety of aldimines by choosing appropriate reaction conditions. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.

AB - The asymmetric Payne oxidation of N-sulfonyl imines catalyzed by a P-spiro chiral triaminoiminophosphorane was developed for the practical synthesis of optically active N-sulfonyl oxaziridines. High efficiency and an excellent level of enantioselectivity were generally achieved with a wide variety of aldimines by choosing appropriate reaction conditions. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.

KW - asymmetric catalysis

KW - oxaziridines

KW - oxidation

KW - peroxides

KW - stereoselective synthesis

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M3 - Article

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JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 7

M1 - 5440

ER -

The practical preparation of chiral N-sulfonyl oxaziridines via catalytic asymmetric payne oxidation

Abstract

Keywords

ASJC Scopus subject areas

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