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Synlett 2012; 23(9): 1374-1378
DOI: 10.1055/s-0031-1291046
DOI: 10.1055/s-0031-1291046
letter
Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles
Weitere Informationen
Publikationsverlauf
Received: 13. März 2012
Accepted: 28. März 2012
Publikationsdatum:
14. Mai 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201209/lookinside/thumbnails/10.1055-s-0031-1291046-1.jpg)
Abstract
The preparation of 5-substituted 2,3-methanopyrrolidines by the stereoselective cyclization of zincated α-amino nitriles derived from enantiopure α-branched homoallylamines has been investigated. The formation of trans adducts in excellent diastereoselectivities (up to >98:2) and good yields (up to 71%) is observed. The absolute configuration and enantiomeric excess are dependent on the nitrogen protecting group.
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