Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles

A highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles has been studied. Deprotonation of 4 with LDA at low temperature affords the corresponding exocyclic lithium enolate 5, which reacts with different electrophiles such as alkyl halides, aldehydes and acyl chlorides to give the corresponding <i>exo</i> addition products 6. The products are formed in good yields and with diastereoselectivities above 95%.