Highly selective synthetic method for 1,6-diols bearing enyne functions: Development of 3,6-dianion reagent of 1,2-hexadien-4-yne using 1,6-dibromo-2,4-hexadiyne and indium

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SCOPUS

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초록

The reaction of aldehydes and ketones with an organoindium reagent generated in, situ from indium and 1,6-dibromo-2,4-hexadiyne in the presence of lithium iodide in tetrahydrofuran (THF) selectively produced 1,6-diols linked to an allenyne unit with complete regioselectivity and chemoselectivity through 1,2-hexadien-4-yn-3,6-ylation, indicating that the organoindium acted as the 3,6-dianion reagent of 1,2-hexadien-4-yne.

키워드

1,6-dibromo-2,4-hexadiyne1,6-diolsenynes1,2-hexadien-4-yn-3,6-ylationindiumCROSS-COUPLING REACTIONSMEDIATED ALLYLATIONAQUEOUS-MEDIAENANTIOSELECTIVE ALLYLATIONORGANOMETALLIC REACTIONSREFORMATSKY REACTIONORGANIC-REACTIONSCARBON-CARBONIN-SITUALDEHYDES
제목
Highly selective synthetic method for 1,6-diols bearing enyne functions: Development of 3,6-dianion reagent of 1,2-hexadien-4-yne using 1,6-dibromo-2,4-hexadiyne and indium
저자
Kim, SundaeLee, KooyeonSeomoon, DongLee, Phil Ho
DOI
10.1002/adsc.200700309
발행일
2007-11
유형
Article
저널명
Journal für Praktische Chemie
349
16
페이지
2449 ~ 2453