75735-33-0Relevant academic research and scientific papers
Asymmetric reduction of α-keto aldoxime o -ethers
Bosiak, Mariusz J.,Pakulski, Marcin M.
experimental part, p. 316 - 324 (2011/03/18)
The catalytic asymmetric reduction of -keto aldoxime O-methyl, O-benzyl, and O-trityl ethers, derived from substituted acetophenones, with borane/oxazaborolidines, by transfer hydrogenation, and with yeast, was studied. The reduction with borane/oxazaborolidines produced the corresponding -hydroxy oxime ethers, -hydroxy hydroxylamine ethers, and -amino alcohols in 39-78% yields and up to 77% ee. The carbonyl group was selectively reduced by transfer hydrogenation with formic acid-triethylamine catalyzed by RhCl[(R,R)-TsDPEN](Ce, and also with yeast, producing -hydroxy oxime ethers, up to 75% ee and 93% ee, respectively. Georg Thieme Verlag Stuttgart New York.
Enantioselective bioreduction of (E)-1-phenyl-1,2-alkanedione 2-(O-methyloxime)
Kreutz, Olyr C.,Segura, Renata C. M.,Rodrigues, J. Augusto R.,Moran, Paulo J. S.
, p. 2107 - 2115 (2007/10/03)
The baker's yeast reduction of (E)-1-phenyl-1,2-alkanedione 2-(O-methyloxime), PhC(O)C(NOMe)R (R=Me, Et, n-Pr, n-Bu), gave the corresponding optically active alcohols PhCH2OHC(NOMe)R in 88-99% enantiomeric excess and 48-75% chemical yield. The
Nitrile-forming Eliminations from Oxime Ethers
Hegarty, Anthony F.,Tuohey, Patrick J.
, p. 1313 - 1317 (2007/10/02)
The oxime ethers (7) and (8) (R = alkyl or aryl) undergo base-catalysed elimination to benzonitriles (3) in water-dioxan (4 : 1) at 25 deg C.The Z-isomer (8Z) reacts via hydroxide-catalysed antiperiplanar elimination 70-fold more rapidly than the corresponding E-isomer.Electronic effects on syn-elimination (from 7E) show that electron-withdrawing groups aid elimination in both Ar and in the leaving group -OR; no intramolecular assistance is observed in these substrates.These results are interpreted in terms of a central E2 elimination, with appreciable C-H and N-O- bond cleavage in the transition state.
