Entry to beta-Alkoxyacrylates via Gold-Catalyzed Intermolecular Coupling of Alkynoates and Allylic Ethers

Park, Sae Rom; Kim, Cheoljae; Kim, Dong-gil; Thrimurtulu, Neetipalli; Yeom, Hyun-Suk; Jun, Jungho; Shin, Seunghoon; Rhee, Young Ho

doi:10.1021/ol4001087

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Entry to beta-Alkoxyacrylates via Gold-Catalyzed Intermolecular Coupling of Alkynoates and Allylic Ethers

Park, Sae Rom;
Kim, Cheoljae;
Kim, Dong-gil;
Thrimurtulu, Neetipalli;
Yeom, Hyun-Suk;
... Shin, Seunghoon;
외 2명

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초록

The first gold-catalyzed Intermolecular coupling of alkynoates and allylic ethers invoking alkoxy addition and [3,3]-sigmatropic rearrangement as the key mechanism has been developed. Remarkably, the reaction showed complete chemoselectivity toward the pathway initiated by the alkoxy addition to alkynes. This unprecedented reactivity led to a new access to diversely substituted beta-alkoxyacrylates in a highly efficient manner.

키워드

INTRAMOLECULAR CARBOALKOXYLATION; GOLD(I)-CATALYZED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CYCLIZATION; COMPLEXES; ALKYNES; LIGAND; CYCLOISOMERIZATION; REARRANGEMENTS; REACTIVITY

제목: Entry to beta-Alkoxyacrylates via Gold-Catalyzed Intermolecular Coupling of Alkynoates and Allylic Ethers

저자: Park, Sae Rom; Kim, Cheoljae; Kim, Dong-gil; Thrimurtulu, Neetipalli; Yeom, Hyun-Suk; Jun, Jungho; Shin, Seunghoon; Rhee, Young Ho

DOI: 10.1021/ol4001087

발행일: 2013-03

유형: Article

저널명: Organic Letters

권: 15

호: 6

페이지: 1166 ~ 1169