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Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis.

ABSTRACT: 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.

SUBMITTER: Hodgson DM

PROVIDER: S-EPMC2587947 | biostudies-literature |

REPOSITORIES: biostudies-literature

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