Abstract
Novel three-component domino processes to polyheterocycles are developed. Reaction of an allylamine ( 3 ), an aldehyde ( 4 ) and an α-isocyanoacetamide ( 5 ) in methanol at room temperature provides an efficient access to oxa-bridged tricycle ( 1 ) as a single diastereoisomer. In this one-pot process, one C–N, one C–O and three C–C bonds are formed with concomitant creation of five asymmetric centers. While isolable, the oxa-bridged tricycles ( 1 ) can be cleanly in-situ fragmented to pyrrolopyridines ( 2 ) under acidic conditions (trifluoroacetic acid, −78°C), providing thus an unusual work-up derived structural diversity. The operational simplicity and excellent chemical yield make these novel heterocycle syntheses valuable in diversity-oriented high throughput synthesis.
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