Gold-catalyzed ring expansions of 1-alkynylcyclobutanol derivatives via tandem hydration and alpha-ketol rearrangement
- Authors
- Kim, Ki-Dae; Yeom, Hyun-Suk; Shin, Sunwoong; Shin, Seunghoon
- Issue Date
- Jul-2012
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- Gold catalysis; alpha-Ketol rearrangement; Ring expansion; Tandem reaction; alpha-Hydroxycyclopentanone
- Citation
- TETRAHEDRON, v.68, no.26, pp.5241 - 5247
- Indexed
- SCIE
SCOPUS
- Journal Title
- TETRAHEDRON
- Volume
- 68
- Number
- 26
- Start Page
- 5241
- End Page
- 5247
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/144739
- DOI
- 10.1016/j.tet.2012.03.018
- ISSN
- 0040-4020
- Abstract
- We report herein the gold-catalyzed tandem hydration/alpha-ketol rearrangement of 1-alkynylcyclobutanol derivatives, leading to cyclopentanones bearing an alpha-hydroxy substituted quaternary center. In the presence of water, coordination of gold catalyst onto alkynyl moiety triggers hydration rather than a direct ring expansion, which followed by unprecedented Au-catalyzed alpha-ketol rearrangement. The details and the scope of this method are presented.
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