Citation
Ta. Ader et al., Polyquinanes by [4+4] cycloaddition-transannular cyclization, ORG LETT, 3(14), 2001, pp. 2165-2167
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060
→ ACNP
Volume
3
Issue
14
Year of publication
2001
Pages
2165 - 2167
Database
ISI
SICI code
1523-7060(20010712)3:14<2165:PB[CC>2.0.ZU;2-8
Abstract
[GRAPHICS]
Photocycloaddition of 2-pyridones yields a rigid polycyclic product contain
ing a 1,5-cyclooctadiene. The cis isomer, with the alkenes in close proximi
ty, undergoes a transannular reaction when treated with chlorine to give a
polyquinane product. The chlorination reaction involves migration of an ami
de nitrogen and forms a single isomer, generating eight stereogenic centers
in two steps.