1201827-38-4Relevant articles and documents
Synthesis and Application of Substituted 1,16-Dihydroxytetraphenylenes in Catalytic Asymmetric Allylboration of Ketones
Chai, Guo-Li,Zhu, Bo,Chang, Junbiao
, p. 120 - 127 (2019/01/08)
The synthesis and application of a newly designed C2-symmetric chiral-substituted 1,16-dihedroxytetraphenylene (DHTP) is reported. Efficient syntheses of enantiopure substituted DHTP were accomplished, and these enantiopure compounds were used as organocatalysts in asymmetric allylboration of ketones under very mild conditions. Accordingly, several tertiary alcohols were generated in moderate to good yields with up to 99% ee by using the catalyst (S)-2,15-Br2-DHTP. A gram-scale reaction was achieved in 99% yield with 96% ee.
One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Br?nsted Acid and Palladium Catalysis
Faggyas, Réka J.,Calder, Ewen D. D.,Wilson, Claire,Sutherland, Andrew
, p. 11585 - 11593 (2017/11/10)
A one-pot catalytic enantioselective allylboration/Mizoroki-Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Br?nsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki-Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.