Synthesis of (R)- and (S)-5-(Hydroxymethyl)-3-isopropyloxazolidin-2-one, intermediates in the preparation of optically active β-blockers
✍ Scribed by Erwin G. J. C. Warmerdam; Johannes Brussee; Arne van der Gen; Chris G. Kruse
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- German
- Weight
- 332 KB
- Volume
- 77
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The (R)‐ and (S)‐5‐(hydroxymethyl)‐3‐isopropyloxazolidin‐2‐ones, ((R)‐ and (S)‐2, resp.), pivotal intermediates in the preparation of optically active β‐blockers, were synthesized using (R,E)‐2‐hydroxypent‐3‐enenitrile (1) as the chiral starting material. In the synthesis of (R)‐2, a known cyclization/inversion step was applied.
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## Abstract Lipase Amano PS is a suitable biocatalyst for the highly regio‐ and enantioselective transesterification of the racemic prostaglandin building block (1__S__~\*~,5__R__\*,6__R__\*,7__R__\*)‐(±)‐7‐hydroxy‐6‐hydroxymethyl‐2‐oxabicyclo[3.3.0]octan‐3‐one (__rac__‐1) yielding (1__S__,5__R__,6
2S,3S)-3-methyl-and 3-isopropylaspartic acids were synthesized by bioconversion of the corresponding alkylfumarates (mesaconate and 3-isopropylfumarate) using pmethylaspartase from cell-free extracts of Clostridium tetanomorphum. Optically pure (2S,3S)-3-alkylaspartic acids were transformed in sever