Indium-mediated regio- and chemoselective synthesis of α-hydroxyalkyl allenic esters and gold-catalyzed cyclizations to ethyl 2-naphthoate derivatives

Park, Chansoo; Lee, Phil Ho

doi:10.1021/ol801196g

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Indium-mediated regio- and chemoselective synthesis of α-hydroxyalkyl allenic esters and gold-catalyzed cyclizations to ethyl 2-naphthoate derivatives

Park, Chansoo;
Lee, Phil Ho

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WEB OF SCIENCE

53

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SCOPUS

58

초록

The regio- and chemoselective synthetic method of functionalized alpha-hydroxyalkyl allenic esters was developed from the reactions of various aldehydes with organoindium reagent generated in situ from indium and ethyl 4-bromobutynoate. The alpha-hydroxyalkyl allenic esters possessing electron-donating groups were cyclized to ethyl 2-naphthoate derivatives through intramolecular C-alkylation catalyzed by gold salts.

키워드

CROSS-COUPLING REACTIONS; ORGANIC-SYNTHESIS; IN-SITU; CARBONYL PROPARGYLATION; ALDEHYDES; CYCLOISOMERIZATION; ALLENYLATION; GOLD(III); BROMIDE; HALIDES

제목: Indium-mediated regio- and chemoselective synthesis of α-hydroxyalkyl allenic esters and gold-catalyzed cyclizations to ethyl 2-naphthoate derivatives

저자: Park, Chansoo; Lee, Phil Ho

DOI: 10.1021/ol801196g

발행일: 2008-08-07

유형: Article

저널명: Organic Letters

권: 10

호: 15

페이지: 3359 ~ 3362