Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: formal syntheses of natural epibatidine and its enantiomer
Moreno-Vargas, A. J.; Vogel, P.
2003

Abstract

The efficient resolution of racemic N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one (+/-)-2 via aminal formation with (R,R)-1,2-diphenylethylenediamine 4 is reported. Acidic hydrolysis furnishes the enantiomeric ketones (+)-2 and (-)-2 that were transformed into 7-azabicyclo[2.2.1]heptan-2-one (-)-3 and (+)-3. The process constitutes a formal synthesis of (+)- and (-)-epibatidine. (C) 2003 Elsevier Ltd. All rights reserved.

Details

Title Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: formal syntheses of natural epibatidine and its enantiomer
Author(s) Moreno-Vargas, A. J. ; Vogel, P.
Published in Tetrahedron-Asymmetry
Volume 14
Issue 20
Pages 3173-3176
Date 2003
ISSN 0957-4166
Keywords
Note Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCH, CH-1015 Lausanne, Switzerland.
DOI https://doi.org/10.1016/j.tetasy.2003.08.021
Other identifier(s) View record in Web of Science
Laboratories LGSA
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2005-11-09

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