Gold-Catalyzed Regioselective Meyer-Schuster Rearrangement and Ring Expansion Cascade Leading to alpha-Hydroxy-alpha-vinylcyclopentanones
- Authors
- An, Jun-Hyun; Yun, Hokeun; Shin, Sunwoong; Shin, Seunghoon
- Issue Date
- Dec-2014
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- allenols; butyne-1,4-diols; gold catalysis; Meyer-Schuster rearrangement; regioselectivity
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.356, no.18, pp.3749 - 3754
- Indexed
- SCIE
SCOPUS
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 356
- Number
- 18
- Start Page
- 3749
- End Page
- 3754
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/143285
- DOI
- 10.1002/adsc.201400569
- ISSN
- 1615-4150
- Abstract
- Readily available cyclobutanols having a butyne-1,4-diol moiety underwent a sequential regioselective Meyer-Schuster rearrangement and 1,2-shift, furnishing alpha-hydroxy-alpha-vinylcyclopentanones. The reaction mechanism is consistent with the formation of an allenol intermediate that racemizes under the reaction conditions. Subsequent activation of the allenol leads to an enantio- and diastereoselective route to this scaffold.
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