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Stereoselective Reducing Complexes Supported in Solid Phase: Preparation and Reactivity Study
Author(s) -
VargasDurazo Judas,
AguilarMartínez Milagros,
OchoaTerán Adrian,
SantacruzOrtega Hisila,
Alonzo Fernando Rocha,
Meza Nohemi Gamez,
GalvezRuiz Juan Carlos
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803644
Subject(s) - enantioselective synthesis , acetophenone , ethylenediamine , chelation , chemistry , denticity , borane , reactivity (psychology) , alcohol , amine gas treating , organic chemistry , stereoselectivity , combinatorial chemistry , polymer chemistry , catalysis , metal , medicine , alternative medicine , pathology
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.