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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

 

作者: Jörg Wilken,   Sabine Wallbaum,   Wolfgang Saak,   Detlef Haase,   Siegfried Pohl,   Jürgen Martens,   Laxmikant N. Patkar,   Arun N. Dixit,   Pabba Chittari,   Srinivasachari Rajappa,  

 

期刊: Liebigs Annalen  （WILEY Available online 1996）
卷期: Volume 1996, issue 6  

页码: 927-934

 

ISSN:0947-3440

 

年代: 1996

 

DOI:10.1002/jlac.199619960610

 

出版商: WILEY‐VCH Verlag

 

关键词: Thio Claisen rearrangement;Proline analogues;Cyclopenta[b]pyrroles;2‐Azabicyclo[3.3.0]octanes

 

数据来源: WILEY

 

摘要:

AbstractUtilization of the industrial waste material benzyl (all‐R)‐cyclopenta[b]pyrrol‐2‐carboxylate1aor its derivatives1b, 1cas chiral auxiliaries is described. Allylation of nitrothioacetamides, proceeding by initialS‐allylation followed by a facile thio Claisen rearrangement, is accomplished with a diastereomeric ratio (dr) up to 85:15 using1a,bas 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 of1awas used as source of

 

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