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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Bibliographic Details
Published inJournal of chemical research. Synopses no. 7; pp. 263 - 264
Main Authors Skarzewski, J, Ostrycharz, E, Siedlecka, R, Zielinska-Blajet, M, Pisarski, B
Format Journal Article
LanguageEnglish
Published NORTHWOOD Science Reviews Ltd 01.07.2001
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Michael addition
OXIDATION
TRANSFORMATION
Schiff bases
sulfoxidation
DIKETENE
TITANIUM ALKOXIDE COMPLEXES
catalysis
ALDEHYDES
SCHIFF-BASE COMPLEXES
enantioselection
ASYMMETRIC CATALYTIC TRIMETHYLSILYLCYANATION
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Summary: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.
ISSN:0308-2342