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

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(07): 871-878
DOI: 10.1055/s-0033-1340818

practical synthetic procedures

The Practical Preparation of Chiral N-Sulfonyl Oxaziridines via Catalytic Asymmetric Payne Oxidation

Ryosuke Tsutsumi

^aInstitute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan

,

Seonwoo Kim

^aInstitute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan

,

Daisuke Uraguchi

^aInstitute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan

,

Takashi Ooi*

^aInstitute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan

^bCREST, Japan Science and Technology Agency (JST), Chikusa, Nagoya 464-8603, Japan Fax: +81(52)7893338 eMail: tooi@apchem.nagoya-u.ac.jp

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Abstract

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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.

Key words

asymmetric catalysis - oxaziridines - oxidation - peroxides - stereoselective synthesis

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Referenzen

References
1 Present address: Department of Chemistry, Seoul National University, Seoul 151-747, Republic of Korea.

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