Eight chelating resins were synthesized in high yields by supporting 2‐aminomethylpyridine, 2,2′‐dipyridylamine, 1,2‐phenylenediamine and 1,2‐ethylenediamine on Merrifield and Wang resins, respectively. These resins were used both as support of reducing complexes and as alkali metal sensors. 16 stable and easy to prepare reducing complexes, derived from the chelating resins and LiBH4 and NaBH4, were prepared in good yields. These complexes showed chemoselectivity to reduce aldehydes in a low molar ratio and short time reactions. The fluorescence‐sensing behavior of the chelating resins for alkali metal was studied. The fluorescence response of the materials where 1, 2‐phenylenediamine is supported on Merrifield and Wang resins indicate that they behave as sensors for Li+and K+, respectively.
Twelve new chiral chelating resins have been prepared using solid phase organic synthesis with the Merrifield and Wang resins and the bidentate amine 1,2‐ethylenediamine, followed by the coupling of asymmetric ketones such as 1‐phenyletanone, 4‐methyl‐2‐pentanone 4‐nitroacetophenone and 4‐methoxyacetophenone to form prochiral imines. The enantioselective reduction with borane and (R)‐(+)‐2‐Methyl‐CBS‐oxazaborolidine leads to the chiral resins with yields greater than 86%. We used these chiral resins to prepare 24 reducing complexes with alkali tetrahydroborates in a very simple way giving yields greater than 87%. Finally, we achieved a preliminary enantioselective reduction of acetophenone employing the Merrifield's chiral chelating resins obtaining the corresponding S alcohol in a 70:30 ratio with the R analog alcohol.
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