121039-98-3Relevant articles and documents
Highly Selective One-Pot Synthesis of Polysubstituted Isoflavanes using Styryl Ethers and Electron-Withdrawing ortho -Quinone Methides Generated in Situ
Tanaka, Kenta,Kishimoto, Mami,Ohtsuka, Naoya,Iwama, Yoshinori,Wada, Hiroki,Hoshino, Yujiro,Honda, Kiyoshi
, p. 189 - 192 (2019)
A highly selective one-pot synthesis of polysubstituted isoflavanes has been developed. The reaction proceeds through the cycloaddition of methyl styryl ethers, derived from phenylacetaldehyde dimethyl acetals under acidic conditions, with electron-withdrawing ortho -quinone methides generated in situ. When phenylacetaldehyde dimethyl acetals were reacted with salicylaldehydes, the reaction proceeded smoothly to afford the corresponding isoflavanes stereoselectively in high yields and with excellent regioselectivities. The present reaction provides versatile access to functionalized isoflavanes, and constitutes a useful tool for the synthesis of biologically active molecules.
Hypoiodous acid-catalyzed regioselective geminal addition of methanol to vinylarenes: synthesis of anti-Markovnikov methyl acetals
Peraka, Swamy,Mameda, Naresh,Marri, Mahender Reddy,Kodumuri, Srujana,Chevella, Durgaiah,Sripadi, Prabhakar,Nama, Narender
, p. 73732 - 73736 (2015/09/15)
A novel metal-free, catalytic geminal dimethoxylation of vinylarenes based on in situ generated HOI species from iodide salt and oxone is reported. The preliminary mechanistic investigations suggest that the key factor for achieving the anti-Markovnikov regioselectivity is the semipinacol rearrangement of an iodo functionalized intermediate, which is confirmed by an isotope labeling experiment. In addition, the reaction involves the de-iodination of a co-iodo intermediate via its oxidation to hypervalent iodine species rather than a common iodide abstraction by electrophiles. The HRESI-MS studies support the conversion of monovalent iodine containing intermediates to trivalent iodine intermediates during the catalytic conversion of aromatic alkenes into the corresponding terminal acetals.