1201651-97-9Relevant articles and documents
p-Methylbenzyl 2,2,2-Trichloroacetimidate: Simple Preparation and Application to Alcohol Protection
Arai, Tomoki,Ikeuchi, Kazutada,Murasawa, Kentaro,Yamada, Hidetsohi
, p. 1034 - 1037 (2020)
A method for p-methylbenzyl (MBn) protection of alcohols by using MBn 2,2,2-trichloroacetimidate is described. The trichloroacetimidate can easily be prepared and isolated as a stable white powder without purification by silica gel chromatography. Catalytic use of zinc(II) triflate in diethyl ether activates the trichloroacetimidate to enable MBn protection of various alcohols.
P-Methylbenzyl Group: Oxidative Removal and Orthogonal Alcohol Deprotection
Ikeuchi, Kazutada,Murasawa, Kentaro,Ohara, Kenya,Yamada, Hidetoshi
supporting information, p. 6638 - 6642 (2019/09/30)
We describe the practical removal of p-methylbenzyl (MBn) protections of alcohols by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone. When a molecule bears benzyl and MBn groups, the oxidant selectively removes the latter groups. Further, the MBn groups tolerate ceric ammonium nitrate, resulting in chemoselective removal of the p-methoxybenzyl group in the presence of the MBn groups. These orthogonal alcohol deprotections would provide novel synthetic strategies of organic compounds.
Reductive Etherification via Anion-Binding Catalysis
Zhao, Chenfei,Sojdak, Christopher A.,Myint, Wazo,Seidel, Daniel
supporting information, p. 10224 - 10227 (2017/08/10)
Reductive condensations of alcohols with aldehydes/ketones to generate ethers are catalyzed by a readily accessible thiourea organocatalyst that operates in combination with HCl. 1,1,3,3-tetramethyldisiloxane serves as a convenient reducing reagent. This strategy is applicable to challenging substrate combinations and exhibits functional group tolerance. Competing reductive homocoupling of the carbonyl component is suppressed.
Synthesis of dialkyl ethers from organotrifluoroborates and acetals
Mitchell, T. Andrew,Bode, Jeffrey W.
supporting information; experimental part, p. 18057 - 18059 (2010/03/26)
(Chemical Equation Presented) The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF3?OEt2