Synlett 2012; 23(9): 1374-1378
DOI: 10.1055/s-0031-1291046
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles

Sabrina Ouizem
UPMC – Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), Institut de Chimie Moléculaire (FR 2769), Case 183, 4 Place Jussieu 75252 Paris Cedex 05, France, Fax: +33(1)44277567   Email: fabrice.chemla@upmc.fr   Email: franck.ferreira@upmc.fr   Email: alejandro.perez_luna@upmc.fr
,
Fabrice Chemla*
UPMC – Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), Institut de Chimie Moléculaire (FR 2769), Case 183, 4 Place Jussieu 75252 Paris Cedex 05, France, Fax: +33(1)44277567   Email: fabrice.chemla@upmc.fr   Email: franck.ferreira@upmc.fr   Email: alejandro.perez_luna@upmc.fr
,
Franck Ferreira*
UPMC – Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), Institut de Chimie Moléculaire (FR 2769), Case 183, 4 Place Jussieu 75252 Paris Cedex 05, France, Fax: +33(1)44277567   Email: fabrice.chemla@upmc.fr   Email: franck.ferreira@upmc.fr   Email: alejandro.perez_luna@upmc.fr
,
Alejandro Perez-Luna*
UPMC – Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), Institut de Chimie Moléculaire (FR 2769), Case 183, 4 Place Jussieu 75252 Paris Cedex 05, France, Fax: +33(1)44277567   Email: fabrice.chemla@upmc.fr   Email: franck.ferreira@upmc.fr   Email: alejandro.perez_luna@upmc.fr
› Author Affiliations
Further Information

Publication History

Received: 13 March 2012

Accepted: 28 March 2012

Publication Date:
14 May 2012 (online)


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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