Publication: New Optically Active 2H-Azirin-3-amines as Synthons for Enantiomerically Pure 2,2-Disubstituted Glycines
New Optically Active 2H-Azirin-3-amines as Synthons for Enantiomerically Pure 2,2-Disubstituted Glycines
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Brun, K. A., Linden, A., & Heimgartner, H. (2001). New Optically Active 2H-Azirin-3-amines as Synthons for Enantiomerically Pure 2,2-Disubstituted Glycines. Helvetica Chimica Acta, 84(6), 1756–1777. https://doi.org/10.1002/1522-2675(20010613)84:6<1756::AID-HLCA1756>3.0.CO;2-J
Abstract
Abstract
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 au
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- Brun, Kathrin A
- Heimgartner, Heinz
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Citations
Brun, K. A., Linden, A., & Heimgartner, H. (2001). New Optically Active 2H-Azirin-3-amines as Synthons for Enantiomerically Pure 2,2-Disubstituted Glycines. Helvetica Chimica Acta, 84(6), 1756–1777. https://doi.org/10.1002/1522-2675(20010613)84:6<1756::AID-HLCA1756>3.0.CO;2-J
