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Selenolactams as Synthetic Intermediates for the Synthesis of Polycyclic Amines via Seleno-Claisen Rearrangements

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posted on 2018-03-01, 00:00 authored by Fumitoshi Shibahara, Masafumi Suzuki, Saki Kubota, Tomoki Fukunaga, Taro Udagawa, Toshiaki Murai
A highly diastereoselective α-allylation of selenolactams with allyl halides is reported. DFT analyses and experimental observations suggested that this reaction proceeds via a Se-allylation of the eneselenolates of the lactams followed by a seleno-Claisen rearrangement. The thus-obtained products could be efficiently transformed into polycyclic amines using a previously developed sequential addition of organometallic reagents and ring-closing metathesis.

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