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.


Published in:
Tetrahedron-Asymmetry, 14, 20, 3173-3176
Year:
2003
ISSN:
0957-4166
Keywords:
Note:
Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCH, CH-1015 Lausanne, Switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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