A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis

作者：Kale Balaji S; Lee Hsin Fu; Liu Rai Shung^*

来源：Advanced Synthesis & Catalysis, 2017, 359(3): 402-409.

DOI：10.1002/adsc.201600980

• cyclopropylgold carbenes
• diazo ketones
• 1,6-enynes
• formal [2+2+1]-cycloaddition
• gold
• rhodium-catalyzed process

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-2en- 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.

• 出版日期2017-2
• 单位清华大学