Complementary chemistry! α-Isocupreine (-ICPN) was synthesized for the first time in one step from quinine by treatment with CF3SO3H (see scheme). This compound serves as an enantiocomplementary catalyst to β-isocupreidine (β-ICD) in the Morita–Baylis–Hillman reaction.
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Chemoenzymatic access to enantiopure N-containing furfuryl alcohol from chitin-derived N-acetyl-D-glucosamine.
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School of Food Science and Engineering, South China University of Technology, 381 Wushan Road, Guangzhou, 510640, China.
Background: Chiral furfuryl alcohols are important precursors for the synthesis of valuable functionalized pyranones such as the rare sugar L-rednose. However, the synthesis of enantiopure chiral biobased furfuryl alcohols remains scarce. In this work, we present a chemoenzymatic route toward enantiopure nitrogen-containing (R)- and (S)-3-acetamido-5-(1-hydroxylethyl)furan (3A5HEF) from chitin-derived N-acetyl-D-glucosamine (NAG).
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Department of Chemistry, Pohang University of Science and Technology, 77 Cheongam-ro, Pohang 37673, Republic of Korea.
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View Article and Find Full Text PDFComplementary chemistry! α-Isocupreine (-ICPN) was synthesized for the first time in one step from quinine by treatment with CF3SO3H (see scheme). This compound serves as an enantiocomplementary catalyst to β-isocupreidine (β-ICD) in the Morita–Baylis–Hillman reaction.
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Kutateladze Institute of Pharmacochemistry, Laboratory of Plant Biopolymers, 0159 Tbilisi, Georgia.
The racemic and enantioselective synthesis of a novel glyceric acid derivative, namely, 2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid as well as the antioxidant activities is described. The virtually pure enantiomers, (+)-(2R,3S)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid and (-)-(2S,3R)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)-propionic acid were synthesized for the first time via Sharpless asymmetric dihydroxylation of trans-caffeic acid derivatives using the enantiocomplementary catalysts, (DHQD)(2)-PHAL and (DHQ)(2)-PHAL. The determination of enantiomeric purity of the novel chiral glyceric acid derivatives was performed by high-performance liquid chromatographic techniques on the stage of their alkylated precursors.
View Article and Find Full Text PDFChiral 2-endo-substituted 9-oxabispidines: novel ligands for enantioselective copper(II)-catalyzed Henry reactions.
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November 2009
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.
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