2000
DOI: 10.1016/s0957-4166(00)00166-x
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Asymmetric glyoxylate-ene reaction catalyzed by C2-symmetric chiral bis(oxazoline)–lanthanide complexes

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Cited by 65 publications
(46 citation statements)
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“…For example, complexes with the general formula Ln(pybox)(A) 3 (A ¼ monodentate anionic ligand) have been shown to catalyze a broad selection of reactions, such as enantioselective Diels-Alder [141] and nitrone cycloadditions [142], Friedel-Craft alkylations [143], asymmetric Mannich-type reactions [144], as well as a variety of ene-reactions [145]. It is important to note that most of these processes are catalyzed by in situ prepared complexes, rather than well-defined species, and thus remain out of the scope of this review.…”
Section: Rare Earth Metal Oxazoline Complexes In Asymmetric Catalysismentioning
confidence: 99%
“…For example, complexes with the general formula Ln(pybox)(A) 3 (A ¼ monodentate anionic ligand) have been shown to catalyze a broad selection of reactions, such as enantioselective Diels-Alder [141] and nitrone cycloadditions [142], Friedel-Craft alkylations [143], asymmetric Mannich-type reactions [144], as well as a variety of ene-reactions [145]. It is important to note that most of these processes are catalyzed by in situ prepared complexes, rather than well-defined species, and thus remain out of the scope of this review.…”
Section: Rare Earth Metal Oxazoline Complexes In Asymmetric Catalysismentioning
confidence: 99%
“…9 Use of less nucleophilic olefins is less effective as evidenced by low levels of enantioselection in the glyoxylate ene reaction. 10 Organometal addition to aldehydes using diethylzinc 11 and allylindium reagents are moderately effective, with the latter providing homollylic alcohols in 92% ee with stoichiometric cerium(III) triflate hydrate. 12 1,2-Addition of phenyllithium or phenylmagnesium bromide to a discrete i-Pr-pybox ruthenium(III)-acrolein complex furnished the allylic alcohol in 63-87% ee.…”
Section: Phmentioning
confidence: 99%
“…24 Desimoni et al reported a thorough investigation of the effects of ionic radius and pybox ligand substituents on the stereoselectivity of this reaction. 38 Interestingly they found that not only the magnitude, but also the absolute sense of the stereoinduction was greatly influenced by the nature of the pybox substituents, namely aryl vs. alkyl, specifically, catalysis with iPr-pybox and Ph-pybox gave products with opposite absolute configuration, despite the ligands having the same absolute configuration.…”
Section: Trisoxazoline Complexesmentioning
confidence: 99%