Hydrolytic and Aminolytic Kinetic Resolution of Terminal Bis-Epoxides

Hydrolytic and aminolytic kinetic resolution of terminal bis-epoxides catalyzed by (salen)­Co^III complexes affords epoxy-diols and N-protected epoxy-amino alcohols with excellent enantio- and diastereoselectivity and good yields. An operationally simple procedure gives instant access to valuable building blocks containing two remote stereocenters in highly enantioenriched form

Hydroformylation of Olefinic Derivatives of Isosorbide and Isomannide

The first time application of hydroformylation on olefinic derivatives of isosorbide and isomannide is shown by which a new carbon–carbon bond is formed. Depending on the ligand and reaction conditions used, the C6 regioisomer <b>a</b> can be obtained in 4:1 ratio and excellent yield, whereas C5 isomer <b>b</b> is achieved in almost complete regioselectivity (46:1) and good yield. In the majority of cases only the <i>exo</i> orientation is observed for the obtained aldehydes, and the method is easily applicable also on a 1 g scale

An NMR and MD Modeling Insight into Nucleation of 1,2-Alkanediols: Selective Crystallization of Lipase-Catalytically Resolved Enantiomers from the Reaction Mixtures

The work on developing a scalable lipase-catalytic method for the kinetic resolution of long-chain 1,2-alkanediols, complemented by crystallization of the pure enantiomers from the reaction mixtures, offered the possibility of a more detailed study of the aggregation of such diols. MD modeling, mass spectrometry, ¹H NMR, and DOSY studies provided a novel insight into the nucleation process. An efficient protocol for stereo- and chemoselective crystallization of (<i>S</i>)-<b>1</b>,2-dodecanediol and related compounds from the crude bioconversion mixtures was developed

Substituted 7‑Amino-5-thio-thiazolo[4,5‑<i>d</i>]pyrimidines as Potent and Selective Antagonists of the Fractalkine Receptor (CX₃CR1)

We have developed two parallel series, A and B, of CX₃CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo­[4,5-<i>d</i>]­pyrimidine core structure, we were able to achieve compounds with high selectivity for CX₃CR1 over the closely related CXCR2 receptor. The structure–activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with α-methyl branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochemical properties, as exemplified by compounds <b>18a</b> and <b>24h</b>. We show the preparation of the first potent and selective orally available CX₃CR1 antagonists