137956-87-7Relevant academic research and scientific papers
Platinum-Catalyzed α,β-Desaturation of Cyclic Ketones through Direct Metal–Enolate Formation
Chen, Ming,Dong, Guangbin
supporting information, p. 7956 - 7961 (2021/03/01)
The development of a platinum-catalyzed desaturation of cyclic ketones to their conjugated α,β-unsaturated counterparts is reported in this full article. A unique diene-platinum complex was identified to be an efficient catalyst, which enables direct metal-enolate formation. The reaction operates under mild conditions without using strong bases or acids. Good to excellent yields can be achieved for diverse and complex scaffolds. A wide range of functional groups, including those sensitive to acids, bases/nucleophiles, or palladium species, are tolerated, which represents a distinct feature from other known desaturation methods. Mechanistically, this platinum catalysis exhibits a fast and reversible α-deprotonation followed by a rate-determining β-hydrogen elimination process, which is different from the prior Pd-catalyzed desaturation method. Promising preliminary enantioselective desaturation using a chiral-diene-platinum complex has also been obtained.
S,S'-Diethyl Dithiomalonate as Ethanol Carbanion Equivalent in Annelation Reactions
Liu, Hsing-Jang,Han, Yongxin
, p. 1484 - 1485 (2007/10/02)
S,S'-Diethyl dithiomalonate 1 undergoes concomitant alkylation reaction and Michael addition with ω-iodo-α,β-unsaturated ketones; the thiomalonate group present in the cyclization products can be easily reduced by Raney nickel to ethanol level.
