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

Wilken, Jörg ; Wallbaum, Sabine ; Saak, Wolfgang ; Haase, Detlef ; Pohl, Siegfried ; Martens, Jürgen ; Patkar, Laxmikant N. ; Dixit, Arun N. ; Chittari, Pabba ; Rajappa, Srinivasachari (1996) 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 Liebigs Annalen, 1996 (6). pp. 927-934. ISSN 0947-3440

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/jlac.19...

Related URL: http://dx.doi.org/10.1002/jlac.199619960610

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.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons.
Keywords:Thio Claisen Rearrangement; Proline Analogues; Cyclopenta[b]pyrroles; 2-Azabicyclo[3.3.0]octanes
ID Code:50342
Deposited On:23 Jul 2011 07:19
Last Modified:23 Jul 2011 07:19

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