Au(I)-Catalyzed Hydrative Rearrangement of 1,1-Diethynylcarbinol Acetates to Functionalized Cyclopentenones and Allenones
- Authors
- Oh, Chang Ho; Karmakar, Swastik
- Issue Date
- Jan-2009
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.74, no.1, pp.370 - 374
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 74
- Number
- 1
- Start Page
- 370
- End Page
- 374
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/177434
- DOI
- 10.1021/jo802103g
- ISSN
- 0022-3263
- Abstract
- Atom-economical syntheses of isomeric 5-acetoxy-2-alkyl-2-cyclopentenones (2) and acetoxymethyl (x-alkylailen ones (3) have been described via Au-catalyzed hydrative rearrangement of 1,1-diethynyl-carbinol acetates (1). In anhydrous condition, Au(I)-catalyzed [3,3]-rearrangement of 1 afforded the 3-alkynylallenyl acetate 4 in low yield. Treatment of 1 with Au(I) catalyst in wet CH2Cl2 produced either 2 or 3 as a major product depending on the temperature, reaction time. and catalyst loading. D has been proposed as an intermediate, which might be formed via Au(I)-induced internal oxacyclization of the intermediate 4 followed by chemoselective nucleophilic attack by the water molecule. Formation of 2 or 3 might be explained via sequential 1,3-dioxole ring opening and gold-promoted 5-endo-dig carbocyclization or simple protonation of the intermediate D, respectively.
- Files in This Item
-
Go to Link
- Appears in
Collections - 서울 자연과학대학 > 서울 화학과 > 1. Journal Articles
![qrcode](https://api.qrserver.com/v1/create-qr-code/?size=55x55&data=https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/177434)
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.