Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis.
Tandem deoxygenation-neophyl-type radical rearrangement-electrophile trapping using xanthates from 7-azabenzonorbornadienes gives 3-exo-substituted 2-aza-5,6-benzonorbornenes, which in some cases undergo isomerisation to (aminomethyl)indenes. The starting xanthates are accessible in good yields and high enantiomeric ratios via asymmetric hydroboration of (aryne/pyrrole-derived) 7-azabenzonorbornadienes. Oxidation (using RuO(4)) and Birch reduction of the 2-aza-5,6-benzonorbornenes provide access to substituted pyrrolidines and tetrahydroindenes, respectively.
Hodgson
David M
DM
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
Winning
Leonard H
LH