Synthesis and biochemical evaluation of highly enantiomerically pure (R,R)- and (S,S)-alexidine

Impact of 2‐Ethylhexyl Stereoisomers on the Electrical Performance of Single‐Crystal Field‐Effect Transistors

“…Stereochemically pure enantiomers ( R / R ) 1 and ( S / S ) 1 were synthesized by introducing chiral side chains with enantiomerically pure 2‐ethylhexyl tosylate under conditions described above for ( rac ) 2 and subsequent chlorination (Figure a). The mesomer ( R / S ) 1 could be preferentially crystallized and isolated from P 1 by solvent diffusion method in CH 3 OH/CHCl 3 (2:1) yielding centimeter‐sized crystals, owing to the lower solubility of the mesomer in contrast to the two enantiomers (Figure S3, Supporting Information).…”

Enantioselective Nickel-Electrocatalyzed Reductive Propargylic Carboxylation with CO2

“…The effectiveness and practicality of our asymmetric electroreductive carboxylation reaction were further illustrated in the enantioselective synthesis of (S,S)-alexidine (Figure 2e). 20 The enantioenriched carboxylic acid 2ar was hydrogenated with a catalytic amount of Pd/C, resulting in the formation of compound 25 in 90% yield with 90% ee. The carboxylic acid group was subsequently converted to an amide and subsequently reduced with borane to produce amine 26.…”

Thieno[3,4-b]thiophene–benzo[1,2-b:4,5-b′]dithiophene-based polymers bearing optically pure 2-ethylhexyl pendants: Synthesis and application in polymer solar cells

“…Reaction of 1with alkyl tosylates, which can be easily derivatized from the corresponding alkyl alcohols, has been used to prepare BDT-based monomers bearing alkoxy pendants[30].According to this strategy, enantiopure (R)-and (S)-2-OH were needed to prepare synthesis[40][41][42][43], asymmetric induction[34,[44][45][46] and enzymatic reactions[38,[47][48][49][50][51], have been reported. However, none of these methods satisfy all of the requirements of high enantiomeric purity, high scalability and simplicity.…”