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A mini-review presents advances in the application of graphene-based materials in catalytic stereoselective synthesis. Examples of chiral organocatalysts and metal complexes immobilized on carbon nanosheets are discussed. [ABSTRACT FROM AUTHOR]

An efficient procedure for the synthesis of new enantiopure pyrrolidine-based sulfides bearing additional nitrogen donors and secondary amines based on a bicyclic 2-azanorbornane skeleton was developed. Their application as ligands in palladium-catalyzed Tsuji-Trost reactions led to high yields and up to 82% ee. [ABSTRACT FROM AUTHOR]

Two approaches to terminal alkynes based on the enantiomerically pure epimers (1S,3R,4R)- and (1S,3S,4R)- 2-azabicyclo[2.2.1]heptane aldehydes were established: i) a non-Wittig route through a dichloroalkene intermediate; and, ii) a Corey-Fuchs approach via dibromoalkene. Among various organometallic reagents tested, the use of n-butyllithium was efficient. The resulting alkynes were fully characterized, and one epimer was used in a click chemistry triazole synthesis. For one of the products containing a bulky N-Boc-proline substituent, the existence of atropisomers was observed. The absolute stereochemistry was determined by electronic circular dichroism spectroscopy (ECD) and optical rotation supported by quantum chemical simulations. [ABSTRACT FROM AUTHOR]