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Synthesis of 2-Alkenyl-Tethered Anilines.

ABSTRACT: Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinyl-magnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C-N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrates with pendant alkenes at the 2-position with excellent trans selectivities.

SUBMITTER: Denmark SE

PROVIDER: S-EPMC6008791 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Synthesis of 2-Alkenyl-Tethered Anilines.

Denmark Scott E SE Chi Hyung Min HM

Synthesis 20170504 13

Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinyl-magnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C- ...[more]

PMID: 29937594

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