130993-47-4Relevant articles and documents
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.
Synthesis of (1',2'-trans)-3-phenyl-1-[2'-(N-pyrrolidinyl)cyclohexyl]pyrrolid-2- ones as κ-selective opiates
Cheng,Lu,Lee,Tam
, p. 758 - 762 (2007/10/02)
(1',2'-trans)-3-Phenyl-1-[2'-(N-pyrrolidinyl)cyclohexyl]pyrrolid-2- ones (1 and 2) and their 3,4-dichlorophenyl analogues (4 and 5) were synthesized as lactam analogues of U-50,488 (I; a κ-opiate analgesic developed by Upjohn Company). Compounds 1 and 2 w
