Highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles

Authors
Alonso, DA Nordin, SJM Andersson, PG
Citation
Da. Alonso et al., Highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles, ORG LETT, 1(10), 1999, pp. 1595-1597
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
10
Year of publication
1999
Pages
1595 - 1597
Database
ISI
SICI code
1523-7060(19991118)1:10<1595:HDRO2E>2.0.ZU;2-R
Abstract
A highly diastereoselective reaction of 2-azanorbornyl enolates with electr ophiles has been studied. Deprotonation of 4 with LDA at low temperature af fords the corresponding exocyclic lithium enolate 5, which reacts with diff erent 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%.