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Palladium-Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy.

ABSTRACT: In this report, a palladium-catalyzed redox-relay Heck process to access optically active alkenylated ?,?-unsaturated lactams is described. 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.

SUBMITTER: Yuan Q

PROVIDER: S-EPMC6731067 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy.

Yuan Qianjia Q Sigman Matthew S MS

Chemistry (Weinheim an der Bergstrasse, Germany) 20190726 46

In this report, a palladium-catalyzed redox-relay Heck process to access optically active alkenylated α,β-unsaturated lactams is described. 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 ...[more]

PMID: 31216370

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