More Like this

1. Non‐Covalent Substrate Directed Enantioselective Heck Desymmetrization of cis ‐Cyclohex‐4‐ene‐1,2‐diol: Synthesis of all cis Chiral 5‐Aryl‐cyclohex‐3‐ene‐1,2‐diols and Mechanistic Investigation

   https://doi.org/10.1002/adsc.201800785  

   Angnes, Ricardo A. ; Thompson, Lee M. ; Mashuta, Mark S. ; Correia, Carlos R. D. ; Hammond, Gerald B. ( August 2018 , Advanced Synthesis & Catalysis)

   Enantioselective substrate directed Heck reactions are desirable for the stereoselective synthesis of complex molecules. However, due to the coordination requirements of both chiral ligands and directing groups, such methodologies are underdeveloped. We report herein the desymmetrization ofmeso(1R,2S)‐cyclohex‐4‐ene‐1,2‐diol in an enantioselective and substrate directed fashion. The method provides allcissubstituted highly functionalized chiral allylic alcohols in a complementary fashion to other Heck protocols.The products were obtained in high enantioselectivities (higher than 95% ee) and moderate to high yields (38–87%). The noncovalent interactions responsible for the directing effect were elucidated through computational examination of relevant minima and transition structures.

   magnified image

    

   more » « less
2. High-Throughput Assay for Enantiomeric Excess Determination in 1,2- and 1,3-Diols and Direct Asymmetric Reaction Screening

   https://doi.org/10.1002/chem.201701923  

   Shcherbakova, Elena G. ; Brega, Valentina ; Lynch, Vincent M. ; James, Tony D. ; Anzenbacher, Jr., Pavel ( July 2017 , Chemistry - A European Journal)
3. Ruthenium(0)‐Catalyzed Cycloaddition of 1,2‐Diols, Ketols, or Diones via Alcohol‐Mediated Hydrogen Transfer

   https://doi.org/10.1002/anie.201709916  

   Sato, Hiroki ; Turnbull, Ben W. H. ; Fukaya, Keisuke ; Krische, Michael J. ( February 2018 , Angewandte Chemie International Edition)

   Merging the characteristics of transfer hydrogenation and carbonyl addition, a broad new class of ruthenium(0)‐catalyzed cycloadditions has been developed. As discussed in this Minireview, fused or bridged bicyclic ring systems are accessible in a redox‐independent manner in C−C bond‐forming hydrogen transfer reactions of diols, α‐ketols, or 1,2‐diones with diverse unsaturated reactants.

    

   more » « less
4. Absolute stereochemical determination of 1,2‐diols via complexation with dinaphthyl borinic acid

   https://doi.org/10.1002/chir.23223  

   Torabi Kohlbouni, Saeedeh ; Sarkar, Aritra ; Zhang, Jun ; Li, Xiaoyong ; Borhan, Babak ( March 2020 , Chirality)

   Rapid derivatization of chiral 1,2‐diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton‐coupled circular dichroic (ECCD) of the naphthyl groups. Aryl‐ and alkyl‐substituted 1,2‐diols derivatized withDBAyield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.

    

   more » « less
5. trans -Diamminebis(1,2-dicyanoethene-1,2-dithiolato)platinum(IV)

   https://doi.org/10.1107/S2414314620009803  

   Siddiqui, Mahaa J. ; Nesterov, Volodymyr V. ; Steidle, Matthew T. ; Smucker, Bradley W. ( July 2020 , IUCrData)

   The title compound, [Pt(C 4 N 2 S 2 ) 2 (NH 3 ) 2 ], represents an octahedral platinum(IV) complex with two trans- ammine and two mnt (mnt = 1,2-dicyanoethene-1,2-dithiolato) ligands. The Pt—N and Pt—S distances are consistent with those in other platinum(IV) complexes. As a result of a slight canting of the coordination of the mnt ligand to the platinum(IV) atom, the nitrile nitrogen atoms are positioned suitably to hydrogen-bond with adjacent ammines. 

   more » « less