Tandem Transformations via Friedel–Crafts Acylation Followed by a Ring-Expansion, Ring-Opening, and Cycloisomerization Sequence

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초록

A tandem synthetic route to a diverse array of cyclic compounds has been developed from Friedel–Crafts acylation of alkynes followed by the microwave irradiation of β-chlorovinyl ketone intermediates. The stereoisomeric β-chlorovinyl ketone intermediates smoothly underwent a thermal α-vinyl enolization and ring expansion to vinyl and carbocyclic furans as well as cyclopetene derivatives in good to excellent yields without the need for any catalysts.

키워드

BETA-CHLOROVINYL KETONES; (E)-BETA-CHLOROVINYL KETONES; FACILE ACCESS; ALLENYL; PATHWAYS
제목
Tandem Transformations via Friedel–Crafts Acylation Followed by a Ring-Expansion, Ring-Opening, and Cycloisomerization Sequence
저자
Kim, Hun Young; Oh, Kyungsoo
DOI
10.1021/acs.orglett.8b03881
발행일
2019-02
유형
Article
저널명
Organic Letters
권
21
호
3
페이지
696 ~ 699