1038435-86-7Relevant academic research and scientific papers
Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals
Saito, Emi,Matsumoto, Yuri,Nakamura, Akihiko,Namera, Yuki,Nakada, Masahisa
, p. 692 - 695 (2018)
The preparation and reactions of ortho-benzoquinone monohemiaminals are described. The oxidative dearomatization of phenols bearing amino alcohol groups induced N-cyclization to afford ortho-benzoquinone monohemiaminals. The N-cyclization stereoselectively affords the product when a chiral amino alcohol is used as the substituent. The chiral ortho-benzoquinone monohemiaminal undergoes stereoselective Diels-Alder reactions with electron-deficient alkenes, as expected, confirming the promising utility of ortho-benzoquinone monohemiaminals.
Highly diastereoselective synthesis of orthoquinone monoketals through λ13-iodane-mediated oxidative dearomatization of phenols
Pouysegu, Laurent,Chassaing, Stefan,Dejugnac, Delphine,Lamidey, Anne-Marie,Miqueu, Karinne,Sotiropoulos, Jean-Marc,Quideau, Stephane
supporting information; experimental part, p. 3552 - 3555 (2009/02/07)
(Chemical Equation Presented) Versatile chiral substrates for asymmetric synthesis are formed through the spiroketalization of phenols with a chiral substituted ethanol unit O-tethered to the ortho position upon treatment with PhI-(OAc)2 (see example; TFE = 2,2,2-tri-fluoroethanol). Intermediates with a six-membered iodine(III)-containing ring (the natural localized molecular orbitals associated with the I-C6 bond are shown) undergo ligand coupling to give the spiroketals.
