Utilization of Industrial Waste Materials, 6. Utilization of Derivatives of the Bicyclic Proline Analog (all-R)-Octahydrocyclopenta[b]pyrrol-2-carboxylic Acid in the Stereoselective Synthesis
✍ Scribed by Wilken, Jörg ;Wallbaum, Sabine ;Saak, Wolfgang ;Haase, Detlef ;Pohl, Siegfried ;Martens, Jürgen ;Patkar, Laxmikant N. ;Dixit, Arun N. ;Chittari, Pabba ;Rajappa, Srinivasachari
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 901 KB
- Volume
- 1996
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
Utilization of the industrial waste material benzyl (all‐R)‐cyclopenta[b]pyrrol‐2‐carboxylate 1a or its derivatives 1b, 1c as chiral auxiliaries is described. Allylation of nitrothioacetamides, proceeding by initial S‐allylation followed by a facile thio Claisen rearrangement, is accomplished with a diastereomeric ratio (dr) up to 85:15 using 1a, b as auxiliaries in stoichiometric amounts. Another aspect of this report is the diastereoselective synthesis of optically active amines, starting from aldehydes, with optical purities (op) up to 99%, Again a derivative of 1a was used as source of chirality.