Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis
- Authors
- Yeom, Hyun-Suk; Koo, Jaeyoung; Park, Hyun-Sub; Wang, Yi; Liang, Yong; Yu, Zhi-Xiang; Shin, Seunghoon
- Issue Date
- Jan-2012
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.134, no.1, pp.208 - 211
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Volume
- 134
- Number
- 1
- Start Page
- 208
- End Page
- 211
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/166560
- DOI
- 10.1021/ja210792e
- ISSN
- 0002-7863
- Abstract
- A gold-catalyzed intermolecular reaction of propiolic acids with alkenes led to a [4 + 2] annulation or enyne cross metathesis. The [4 + 2] annulation proceeds with net cis-addition with respect to alkenes and provides an expedient route to alpha,beta-unsaturated delta-lactones, for which preliminary asymmetric reactions were also demonstrated. For 1,2-disubstituted alkenes, unprecedented enyne cross metathesis occurred to give I,3-dienes in a completely stereospecific fashion. DFT calculations and experiments indicated that the cyclobutene derivatives are not viable intermediates and that the steric interactions during concerted sigma-bond rearrangements are responsible for the observed unique stereospecificity.
- 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/166560)
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.