Journal 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.


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