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. 2007 Jan 18;9(2):215-8.
doi: 10.1021/ol062643a.

Highly efficient synthesis of enantiomerically enriched 2-hydroxymethylaziridines by enzymatic desymmetrization

Jun Young Choi  1 , Richard F Borch
Affiliations

Highly efficient synthesis of enantiomerically enriched 2-hydroxymethylaziridines by enzymatic desymmetrization

Jun Young Choi et al. Org Lett. .

Abstract

Both enantiomers of protected and unprotected 2-hydroxymethylaziridines are efficiently and enantiospecifically synthesized by using a combination of enzymatic and synthetic methods. PPL was used for lipase-catalyzed desymmetrization of N-protected serinol. [reaction: see text].

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Figures

Figure 1
Figure 1
1H NMR experiment: Reaction of 3 with K2CO3 in CD3OD. (1) starting material 3; (2) 10 min reaction, 3 + cyclic intermediate + acyclic intermediate + benzyl alcohol + product 6; (3) 50 min reaction, product 6 + benzyl alcohol. See Scheme 4 for resonance letter assignments.
Scheme 1
Scheme 1
Prochirality of Serinol and transformation to aziridine
Scheme 2
Scheme 2
Desymmetrization of N-Ts-serinol 1a with PPL.
Scheme 3
Scheme 3
Aziridine synthesis from lipase product 2d.
Scheme 4
Scheme 4
Mechanism of deprotection for Aziridine 3.
Scheme 5
Scheme 5
Deprotection reactions of Aziridine 3 and 5.
Scheme 6
Scheme 6
Determination of Absolute Configuration
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References

    1. For reviews on the synthesis and reactions of chiral aziridines, see: Sweeney JB. Chem Soc Rev. 2002;31:247.McCoull W, Davis FA. Synthesis. 2000:1347.Tanner D. Angew Chem. 1994;106:625.Angew Chem Int Ed Engl. 1994;33:599.Müller P, Fruit C. Chem Rev. 2003;103:2905. and references therein.

    1. Kim SK, Jacobsen EN. Angew Chem Int Ed Engl. 2004;43:3952. - PubMed
    1. Gillespie KM, Sanders CJ. J Org Chem. 2002;67:3450. - PubMed

    1. A few direct aziridinations of styrene have been reported: Nishikori H, Katsuki T. Tetrahedron Lett. 1996;37:9245.Li Z, Conser KR, Jacobsen EN. J Am Chem Soc. 1993;115:5326.Evans DA, Faul MM, Bilodeau MT, Anderson BA, Barnes DM. J Am Chem Soc. 1993;115:5328.

    1. Asymmetirc synthesis of 2-hydroxymethylazirine has been briefly reported from chiral amino acid without isolation and characterization: Xu J. Tetrahedron: Asymmetry. 2002;13:1129.

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