Highly Diastereoselective Reaction of
2-Azanorbornyl Enolates with
Electrophiles

Alonso, Diego A.; Nordin, Sofia J. M.; Andersson, Pher G.

doi:10.1021/ol990942c.s001

Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles

https://doi.org/10.1021/ol990942c.s001
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journal contribution

posted on 1999-10-17, 00:00 authored by Diego A. Alonso, Sofia J. M. Nordin, Pher G. Andersson

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%.