Photocyclization of 2-azabicyclo[3.3.0]octane-3-carboxylate derivatives: induced and noninduced diastereoselectivity.
[reaction: see text] The decarboxylative photocyclization of potassium 2-azabicyclo[3.3.0]octanoate ethylene-linked to phthalimide leads to a mixture of two diastereoisomeric products. The overall noninduced diastereoselectivity is remarkably high, indicating a preference of spin-orbit coupling controlled 1,7-biradical combination process. Memory of chirality vanished due to free rotation about the connecting spacer bonds.
Griesbeck
A G
AG
Institute of Organic Chemistry, Greinstrasse 4, D-50939 Köln, Germany. griesbeck@uni-koeln.de
Kramer
W
W
Bartoschek
A
A
Schmickler
H
H