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Palladium-Catalyzed Enantioselective Alkenylation Of Enelactams Using A Relay Heck Strategy.

Qianjia Yuan, Matthew S Sigman
Published 2019 · Chemistry, Medicine
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In this report, we describe a palladium-catalyzed redox relay Heck process to access optically active alkenylated α,β-unsaturated lactams. Under mild reaction conditions, electron-deficient alkenyl triflates and electron-rich alkenyl iodonium salts undergo enantioselective and site-selective coupling with enelactams to deliver the products in high yields and excellent enantioselectivities. Furthermore, the products allow facile access to natural products such as (+)-Calvine and (+)-2-Epicalvine in addition to the bioactive molecule aza-Goniothalamin.
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