57074-37-0Relevant articles and documents
Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis
Ahn, Deok Kyun,Kang, Young Woo,Woo, Sang Kook
, p. 3612 - 3623 (2019/03/11)
An efficient and greener deprotection method for p-methoxybenzyl (PMB) ethers using a metal-free visible light photoredox catalyst and air and ammonium persulfate as the terminal oxidants is presented. Various functional groups and protecting groups were tolerated in the developed method to achieve good to excellent yields in short reaction times. Significantly, the developed method was compatible with PMB ethers derived from primary, secondary, and tertiary alcohols and a gram-scale reaction. Mechanistic studies support a proposed reaction mechanism that involves single electron oxidation of the PMB ether.
An Improved and Convenient New Synthesis of the Pheromone Components of the Tomato Leafminer Tuta absoluta
Puigmartí, Marc,Bosch, Ma Pilar,Guerrero, Angel
, p. 961 - 968 (2015/03/30)
A convenient new synthesis of the two pheromone components of the tomato pest Tuta absoluta in high overall yields and high stereoselectivity (30% yield, E,Z,Z 97% for the major compound and 23% yield, E,Z 99% for the minor component) is reported. The approaches compare favorably with others previously described.
One-pot regio- and stereoselective cyclization of 1,2,n-triols
Zheng, Tao,Narayan, Radha S.,Schomaker, Jennifer M.,Borhan, Babak
, p. 6946 - 6947 (2007/10/03)
A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. Copyright