Photocyclization of 2-azabicyclo[3.3.0]octane-3-carboxylate derivatives: induced and noninduced diastereoselectivity |
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| Authors: | Griesbeck A G Kramer W Bartoschek A Schmickler H |
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| Institution: | Institute of Organic Chemistry, Greinstrasse 4, D-50939 K?ln, Germany. griesbeck@uni-koeln.de |
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| Abstract: | reaction: see text] The decarboxylative photocyclization of potassium 2-azabicyclo3.3.0]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. |
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