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research article
Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: formal syntheses of natural epibatidine and its enantiomer
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.
Type
research article
Web of Science ID
WOS:000186083500013
Authors
Publication date
2003
Published in
Volume
14
Issue
20
Start page
3173
End page
3176
Note
Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCH, CH-1015 Lausanne, Switzerland.
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
November 9, 2005
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