ol990942c_si_001.pdf (79.96 kB)
Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles
journal contribution
posted on 1999-10-17, 00:00 authored by Diego A. Alonso, Sofia J. M. Nordin, Pher G. AnderssonA 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%.