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 exo addition products 6. The products are formed in good yields and with diastereoselectivities above 95%.