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

A G Griesbeck; W Kramer; A Bartoschek; H Schmickler

doi:10.1021/ol006943i

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

Org Lett. 2001 Feb 22;3(4):537-9. doi: 10.1021/ol006943i.

Authors

A G Griesbeck¹, W Kramer, A Bartoschek, H Schmickler

Affiliation

¹ Institute of Organic Chemistry, Greinstrasse 4, D-50939 Köln, Germany. [email protected]

PMID: 11178819
DOI: 10.1021/ol006943i

Abstract

[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.