A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite

Saori Kitagawa; Hiromitsu Mori; Tatsuya Odagiri; Katsuya Suzuki; You Kikkawa; Rie Osugi; Shinobu Takizawa; Yoshikazu Kimura; Masayuki Kirihara

doi:10.1055/s-0037-1611722

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CC BY-ND-NC 4.0 · SynOpen 2019; 03(01): 21-25
DOI: 10.1055/s-0037-1611722

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A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite

Saori Kitagawa

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan eMail: kirihara.masayuki@sist.ac.jp

,

Hiromitsu Mori

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan eMail: kirihara.masayuki@sist.ac.jp

,

Tatsuya Odagiri

^bR&D Department of Chemicals, Nippon Light Metal Company, Ltd., Kambara, Shimizu-ku, Shizuoka 421-3203, Japan

,

Katsuya Suzuki

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan eMail: kirihara.masayuki@sist.ac.jp

,

You Kikkawa

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan eMail: kirihara.masayuki@sist.ac.jp

,

Rie Osugi

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan eMail: kirihara.masayuki@sist.ac.jp

,

Shinobu Takizawa

^cThe Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan

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Yoshikazu Kimura

^dResearch and Development Department, Iharanikkei Chemical Industry Co. Ltd., Kambara, Shimizu-ku, Shizuoka 421-3203, Japan

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Masayuki Kirihara *

^aDepartment of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan eMail: kirihara.masayuki@sist.ac.jp

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Abstract

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Abstract

N-Sulfonyloxaziridines (Davis’ oxaziridines) can be synthesized by reacting the corresponding N-sulfonylimines with aqueous sodium hypochlorite in acetonitrile without any catalyst. The pH of the aqueous sodium hypochlorite is crucial to obtain the product in high yield. Optimized conditions are presented that allow synthetically useful Davis’ oxaziridines to be easily obtained in up to 90% yields from the corresponding imines by using inexpensive, stable, environmentally friendly sodium hypochlorite pentahydrate crystals as the oxidant, with high reproducibility.

Key words

oxaziridine - Davis’ oxaziridine - sodium hypochlorite - sodium hypochlorite pentahydrate - N-sulfonylimine - oxidation

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Referenzen

References and Notes

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6 Given that addition of 10 mol% tetrabutylammonium hydroxide (Bu₄NOH) accelerated the oxidation reaction in a biphasic solvent system using trifluoromethylbenzene (benzotrifluoride, BTF), the reaction might proceed enantioselectively if an optically pure alkylammonium salt was employed. As a preliminary result, the desired product 2a was obtained with 7% ee when the reaction was conducted using N-benzylcinchonidinium chloride.