A Sequential Route to Cyclopentenes from 1, 6‐Enynes and Diazo Ketones through Gold and Rhodium Catalysis. Issue 3 (18th January 2017)

• Record Type: Journal Article
• Authors: Kale, Balaji S.; Lee, Hsin‐Fu; Liu, Rai‐Shung
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 3(2017)
• Page Start: 402
• Page End: 409
• Publication Date: 2017-01-18
• Subjects: cyclopropylgold carbenes -- diazo ketones -- 1, 6-enynes -- formal [2+2+1]-cycloaddition -- gold -- rhodium-catalyzed process; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600980
• Languages: English
• ISSNs: 1615-4150

Abstract

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. Abstract :