152667-62-4Relevant articles and documents
Enantioselective Construction of Quaternary Carbon Stereocenter via Palladium-Catalyzed Asymmetric Allylic Alkylation of Lactones
Li, Xiao-Hui,Wan, Shi-Li,Chen, Di,Liu, Qing Rong,Ding, Chang-Hua,Fang, Ping,Hou, Xue-Long
, p. 1568 - 1572 (2016)
An efficient and practical method for the synthesis of α,α-disubstituted six-membered lactones was developed. Enantioselective construction of quaternary carbon centers by utilizing Pd-catalyzed asymmetric allylic alkylation proved its feasibility.
A C=O???Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols
Greenhalgh, Mark D.,Smith, Samuel M.,Walden, Daniel M.,Taylor, James E.,Brice, Zamira,Robinson, Emily R. T.,Fallan, Charlene,Cordes, David B.,Slawin, Alexandra M. Z.,Richardson, H. Camille,Grove, Markas A.,Cheong, Paul Ha-Yeon,Smith, Andrew D.
supporting information, p. 3200 - 3206 (2018/02/22)
A combination of experimental and computational studies have identified a C=O???isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea-catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s factors up to >200). The reaction proceeds at low catalyst loadings (generally 1 mol %) with either isobutyric or acetic anhydride as the acylating agent under mild conditions.
A convenient synthesis of 3-aryl-δ-lactones
Rosen, Jonathan D.,Nelson, Todd D.,Huffman, Mark A.,McNamara, James M.
, p. 365 - 368 (2007/10/03)
Various (±)-3-aryl-δ-lactones have been prepared from the corresponding arylacetic acids. The lithium dianion of the acid is alkylated with 1-bromo-3-chloropropane and the unpurified product is cyclized with DBU in typically ca. 80% yield over both steps.
