Substituted N-salicylidene beta-aminoalcohols: preparation and use as chiral ligands in enantioselective sulfoxidation and conjugate addition
A high yielding synthesis of optically active 3,5-disubstituted salicylidene beta -amino alcohols (6) is described. The catalytic use of D or L-N-(3-phenyl-5-nitrosalicylidene)valinol in enantioselective sulfoxidation (H2O2 / VO(acac)(2)) gives up to 95% e.e. Asymmetric conjugate addition of thiophe...
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Published in | Journal of chemical research. Synopses no. 7; pp. 263 - 264 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
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Science Reviews Ltd
01.07.2001
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Abstract | A high yielding synthesis of optically active 3,5-disubstituted salicylidene beta -amino alcohols (6) is described. The catalytic use of D or L-N-(3-phenyl-5-nitrosalicylidene)valinol in enantioselective sulfoxidation (H2O2 / VO(acac)(2)) gives up to 95% e.e. Asymmetric conjugate addition of thiophenol to 2-cyclohexen-1-one catalysed by Ti(OPr-i)(4) and 6 leads to maximum 31% e.e. in the product. |
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AbstractList | A high yielding synthesis of optically active 3,5-disubstituted salicylidene beta -amino alcohols (6) is described. The catalytic use of D or L-N-(3-phenyl-5-nitrosalicylidene)valinol in enantioselective sulfoxidation (H2O2 / VO(acac)(2)) gives up to 95% e.e. Asymmetric conjugate addition of thiophenol to 2-cyclohexen-1-one catalysed by Ti(OPr-i)(4) and 6 leads to maximum 31% e.e. in the product. |
Author | Zielinska-Blajet, M Skarzewski, J Siedlecka, R Pisarski, B Ostrycharz, E |
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Keywords | Michael addition OXIDATION TRANSFORMATION Schiff bases sulfoxidation DIKETENE TITANIUM ALKOXIDE COMPLEXES catalysis ALDEHYDES SCHIFF-BASE COMPLEXES enantioselection ASYMMETRIC CATALYTIC TRIMETHYLSILYLCYANATION |
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References | CRAWFORD, M (WOS:A1956WK65200045) 1956 TROST, BM (WOS:A1975AG26800040) 1975; 40 Jiang, YZ (WOS:A1995TM38600011) 1995; 6 Bolm, C (WOS:A1997WN73600034) 1997; 117 Vetter, AH (WOS:000072366000026) 1998; 39 Bolm, C (WOS:000078005900011) 1998 Cogan, DA (WOS:000075553400001) 1998; 120 Bolm, C (WOS:A1996TP36800006) 1995; 34 CASIRAGHI, G (WOS:A1980KH44200004) 1980 HAYASHI, M (WOS:A1994NF66700012) 1994; 50 HAYASHI, M (WOS:A1995RU27900003) 1995; 6 BOIVIN, J (WOS:A1992JK10300018) 1992; 33 Oguni, N (WOS:000077080000027) 1998; 39 Skarzewski, J (WOS:000083275600001) 1999; 10 HAYASHI, M (WOS:A1995TD21600012) 1995; 6 JIANG, YZ (WOS:A1995QK51400025) 1995; 6 VANDOORN, AR (WOS:A1991FE81700023) 1991; 56 |
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Snippet | A high yielding synthesis of optically active 3,5-disubstituted salicylidene beta -amino alcohols (6) is described. The catalytic use of D or... |
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Title | Substituted N-salicylidene beta-aminoalcohols: preparation and use as chiral ligands in enantioselective sulfoxidation and conjugate addition |
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