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- Title
A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis.
- Authors
Kale, Balaji S.; Lee, Hsin ‐ Fu; Liu, Rai ‐ Shung
- Abstract
This work reports the construction of cyclopentene cores from 1,6-enynes and aryl diazo ketones through two new reaction sequences involving initial gold-catalyzed cyclization of 1,6-enynes with diazo species, followed by rhodium-catalyzed skeletal rearrangement of the resulting 3-cyclopropyl-2-en-1-ones. In most instances the rhodium-catalyzed reactions afforded cyclopentene derivatives whereas several n-alkyl- or ortho-substituted phenyl ketones delivered seven-membered oxacycles. A plausible mechanism provides rationales for these two distinct products.
- Subjects
ORGANIC compounds; SEQUENTIAL analysis; ENYNES; RHODIUM catalyst selectivity; PHYSICAL &; theoretical chemistry
- Publication
Advanced Synthesis & Catalysis, 2017, Vol 359, Issue 3, p402
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600980