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New Optically Active 2H-Azirin-3-amines as Synthons for Enantiomerically Pure 2,2-Disubstituted Glycines


Brun, Kathrin A; Linden, Anthony; Heimgartner, Heinz (2001). New Optically Active 2H-Azirin-3-amines as Synthons for Enantiomerically Pure 2,2-Disubstituted Glycines. Helvetica Chimica Acta, 84(6):1756-1777.

Abstract

The synthesis of novel 2,2-disubstituted 2H-azirin-3-amines with a chiral amino group is described. Chromatographic separation of the diastereoisomer mixture yielded the pure diastereoisomers (1'R,2R)-4a-e and (1'R,2S)-4a-e (Scheme 1, Table 1), which are synthons for the (R)- and (S)-isomers of isovaline, 2- methylvaline, 2-cyclopentylalanine, 2-methylleucine, and 2-(methyl)phenylalanine, respectively. The configuration at C(2) of the synthons was determined by X-ray crystallography relative to the known configuration of the chiral auxiliary group. The reaction of 4 with thiobenzoic acid, benzoic acid, and the dipeptide Z-Leu-Aib-OH (12) yielded the monothiodiamides 10, the diamides 11 (Scheme 2, Table 3), and the tripeptides 13 (Scheme 3, Table 4), respectively.

Abstract

The synthesis of novel 2,2-disubstituted 2H-azirin-3-amines with a chiral amino group is described. Chromatographic separation of the diastereoisomer mixture yielded the pure diastereoisomers (1'R,2R)-4a-e and (1'R,2S)-4a-e (Scheme 1, Table 1), which are synthons for the (R)- and (S)-isomers of isovaline, 2- methylvaline, 2-cyclopentylalanine, 2-methylleucine, and 2-(methyl)phenylalanine, respectively. The configuration at C(2) of the synthons was determined by X-ray crystallography relative to the known configuration of the chiral auxiliary group. The reaction of 4 with thiobenzoic acid, benzoic acid, and the dipeptide Z-Leu-Aib-OH (12) yielded the monothiodiamides 10, the diamides 11 (Scheme 2, Table 3), and the tripeptides 13 (Scheme 3, Table 4), respectively.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2001
Deposited On:23 Oct 2013 06:39
Last Modified:05 Apr 2016 17:03
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Stiftung für wissenschaftliche Forschung an der Universität Zürich, Stipendienfonds der Basler Chemischen Industrie
Publisher DOI:https://doi.org/10.1002/1522-2675(20010613)84:6<1756::AID-HLCA1756>3.0.CO;2-J

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