Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones

Man-Jin Suh; Sang Woo Kim; Seong In Beak; Hyun-Joon Ha; Won Koo Lee

doi:10.1055/s-2004-815444

LETTER

Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones

Man-Jin Suh^a, Sang Woo Kim^a,b, Seong In Beak^a, Hyun-Joon Ha*^a,b, Won Koo Lee*^c
^a Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Kyunggi-Do 449-719, Korea
Fax: +82(31)3304566; e-Mail: hjha@hufs.ac.kr;
^b Center for Bioactive Molecular Hybrids, Yonsei University, Seoul 120-749, Korea
^c Department of Chemistry, Sogang University, Seoul 121-742, Korea
Fax: +82(2)7010967.; e-Mail: +wonkoo@sogang.ac.kr;

Abstract

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Abstract

The addition of alkyl- and arylmagnesium reagents to chiral [1′(R)-α-methylbenzyl]aziridine-2(R)-carboxaldimines was carried out in a highly stereoselective manner to give 2-aminomethylaziridine. Further treatment of 2-aminomethylaziridines with triphosgene and NaH afforded enantiopure 5-alkyl- or 5-aryl-4-chloromethylimidazolidin-2-ones.

Key words

stereoselectivity - addition reactions - organometallic reagents - aziridines - imines

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References

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