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Title
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Thiourea derivatives of Troger's base: synthesis, enantioseparation and evaluation in organocatalysis of Michael addition to nitroolefins
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Author
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Abstract
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| The catalytic activity of racemic thiourea derivatives of Troger's base (+/-)-2-4 in Michael additions of malonate derivatives to trans-beta-nitrostyrene was studied. Due to the low basicity of Troger's base, the outcome of the addition reactions was strongly dependent on the pK(a) of the nucleophile. Thiourea catalysts (+/-)-2, 3 were resolved on the chiral stationary phase Whelk O1. Unfortunately, enantiopure catalysts 2 and 3 showed no stereoselectivity in the Michael addition. |
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Language
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English
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Source (journal)
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Arkivoc : online journal of organic chemistry. - Place of publication unknown, 2000, currens
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Publication
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Place of publication unknown
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2009
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ISSN
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1551-7004
[print]
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DOI
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10.3998/ARK.5550190.0010.E12
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Volume/pages
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Part 14
(2009)
, p. 124-134
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ISI
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000277913400012
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Full text (Publisher's DOI)
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Full text (open access)
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