1999
DOI: 10.1016/s0040-4039(98)02587-8
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Rigid aminoalcohol backbone as a highly defined chiral template for the preparation of optically active tertiary α-hydroxyl acids

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Cited by 69 publications
(16 citation statements)
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“…Then we tested the catalytic performance of prolinamides 4a – c in asymmetric aldol reactions of acetone 5a with α-ketoesters 6a – g . The reaction products, chiral α-hydroxy-γ-ketoesters 7 , are used as precursors for the synthesis of natural compounds and ingredients of pharmaceutically valuable compositions. Known organocatalysts usually exhibit only a moderate enantioselectivity in these reactions. The enantioselectivity can be improved by carrying out the reactions at a lower reaction temperature (−20 to −30 °C) and/or in the presence of an excess acidic cocatalyst, although the latter significantly complicates recycling of binary catalytic systems. Efficient supported organocatalysts for asymmetric cross-aldol reactions between two ketone molecules have not been reported so far.…”
Section: Resultsmentioning
confidence: 99%
“…Then we tested the catalytic performance of prolinamides 4a – c in asymmetric aldol reactions of acetone 5a with α-ketoesters 6a – g . The reaction products, chiral α-hydroxy-γ-ketoesters 7 , are used as precursors for the synthesis of natural compounds and ingredients of pharmaceutically valuable compositions. Known organocatalysts usually exhibit only a moderate enantioselectivity in these reactions. The enantioselectivity can be improved by carrying out the reactions at a lower reaction temperature (−20 to −30 °C) and/or in the presence of an excess acidic cocatalyst, although the latter significantly complicates recycling of binary catalytic systems. Efficient supported organocatalysts for asymmetric cross-aldol reactions between two ketone molecules have not been reported so far.…”
Section: Resultsmentioning
confidence: 99%
“…A similar approach was used by Senanayake, Fang and co-workers to prepare tertiary α-hydroxy acids. 57 In this case, additions of Grignard reagents to cis-aminoindanol-derived keto esters were explored. Reaction of phenyl ketone 110 with cyclohexylmagnesium bromide in the presence of zinc chloride gave an 84 : 16 mixture of diastereoisomeric adducts from which 111 could be obtained in 55% yield after recrystallisation (Scheme 32).…”
Section: Addition To C᎐ ᎐ O and C᎐ ᎐ N Bondsmentioning
confidence: 99%
“…Aminolytic kinetic resolution (AKR) of racemic epoxides is a simple, convenient, and highly efficient method to prepare highly valuable enantio-pure β-amino alcohols and corresponding chiral epoxides in one go. Driven by the potential application of chiral β-amino alcohols and epoxides, the last couple of decades have seen a spurt of excellent reports on the use of chiral salen complexes of various metal ions for the synthesis of these molecules. , …”
Section: Introductionmentioning
confidence: 99%