Photocyclization of 2-azabicyclo[3.3.0]octane-3-carboxylate derivatives: Induced and noninduced diastereoselectivity

Authors
Griesbeck, AG Kramer, W Bartoschek, A Schmickler, H
Citation
Ag. Griesbeck et al., Photocyclization of 2-azabicyclo[3.3.0]octane-3-carboxylate derivatives: Induced and noninduced diastereoselectivity, ORG LETT, 3(4), 2001, pp. 537-539
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
4
Year of publication
2001
Pages
537 - 539
Database
ISI
SICI code
1523-7060(20010222)3:4<537:PO2DI>2.0.ZU;2-1
Abstract
The decarboxylative photocyclization of potassium 2-azabicyclo[3.3.0]octano ate ethylene linked to phthalimide reads to a mixture of two diastereoisome ric products. The overall noninduced diastereoselectivity is remarkably hig h, indicating a preference of spin-orbit coupling controlled 1,7-biradical combination process, Memory of chirality vanished due to tree rotation abou t the connecting spacer bonds.