Chemie von Aziridincarbonsäuren, V. Asymmetrische Synthese enantiomerenreiner Aziridincarbonsäurederivate aus (R)- und (S)-Glycerinaldehyd-acetonid
✍ Scribed by Ambrosi, Horst-Dieter ;Duczek, Wolfram ;Ramm, Matthias ;Gründemann, Egon ;Schulz, Burkhard ;Jähnisch, Klaus
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 592 KB
- Volume
- 1994
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Chemistry of Aziridine Carboxylic Acids, V. – Asymmetric Synthesis of Enantiomerically Pure Aziridine Carboxylic Acid Derivatives from (R)‐ and (S)‐Glyceraldehyde Acetonide
The α‐bromoacrylic acid derivatives 2 reacted with benzylamine by ring closure to cis‐aziridines 3 and trans‐aziridines 4 with ≥99% diastereomeric excess. The aziridines 3 and 4 were hydrogenated by LiAlH~4~ to give alcohols 5 and 6. Tosylations of 6 yielded the crystalline sulfonamides 7. The absolute configurations of (2__R__,3__S__,4__R__)‐3c, (2__S__,3__R__,4__S__)‐5and (1__R__,2__R__,4__R__)‐7 were determined by X‐ray analyses.