857974-40-4Relevant academic research and scientific papers
Control of the regio- and stereoselectivity in Diels-Alder reactions with quinone boronic acids
Redondo, Maria C.,Veguillas, Marcos,Ribagorda, Maria,Carreno, M. Carmen
, p. 370 - 374 (2009)
(Chemical Equation Presented) It all adds up: The dienophilic reactivity of 2-methyl-substituted quinones has been substantially increased by the introduction of a boronic acid substituent, which makes them equivalent to a highly reactive quinone. The Diels-Alder reactions of these quinones are followed by spontaneous and stereoselective protodeboronation to give the trans-fused adducts. The boron group is a temporal regiocontroller and leads to the uncommon meta adduct.
