2174-58-5Relevant articles and documents
THE TOTAL SYNTHESIS OF PIPTOSIDIN
Poss, A. J.,Smyth, M. S.
, p. 5469 - 5472 (1987)
The synthesis of piptosidin, 2a, by the Michael addition of ascorbic acid to tigloyl cyanide is reported.
Rapid and Efficient Isolation of the Nicotinic Receptor Antagonist Methyllycaconitine from Delphinium: Assignment of the Methylsuccinimide Absolute Stereochemistry as S
Coates, Philippa A.,Blagbrough, Ian S.,Hardick, David J.,Rowan, Michael G.,Wonnacott, Susan,Potter, Barry V. L.
, p. 8701 - 8704 (1994)
Methyllycaconitine (MLA) has been isolated from Garden Hybrid Delphinium and purified by vacuum liquid chromatography. 13C NMR and optical rotation has been used to characterize the absolute configuration of the methylsuccinimide moiety as S.Ligand binding assays confirmed the potency of MLA and its selectivity for α-bungarotoxin-sensitive neuronal nicotinic acetylcholine receptors.
Preparation of Both Enantiomers of Malic and Citramalic Acid and Other Hydroxysuccinic Acid Derivatives by Stereospecific Hydrations of cis or trans 2-Butene-1,4-dioic Acids with Resting Cells of Clostridium formicoaceticum
Eck, Richard,Simon, Helmut
, p. 13641 - 13654 (1994)
(R)-Malic, (S)-malic, (R)-citramalic, (S)-citramalic, (2R,3S)-2-hydroxy-3-methylsuccinic and (2R,3S)-2,3-dimethyl-2-hydroxysuccinic acid were prepared on scales up to 25 mmol by stereospecific addition of water to different 2-butene-1,4-dioic acid derivatives catalyzed by resting cells of Clostridium formicoaceticum (Scheme 1).The (3R)-monodeuterio (R)- and (S)-malic acid as well as (R)- and (S)-citramalic acid were prepared using freeze-dried cells in 2H2O-buffer.The stereochemical purity of the products was in most cases >/= 99percent.
Enantiospecific C-H Activation Using Ruthenium Nanocatalysts
Taglang, Céline,Martínez-Prieto, Luis Miguel,Del Rosal, Iker,Maron, Laurent,Poteau, Romuald,Philippot, Karine,Chaudret, Bruno,Perato, Serge,Sam Lone, Ana?s,Puente, Céline,Dugave, Christophe,Rousseau, Bernard,Pieters, Grégory
supporting information, p. 10474 - 10477 (2015/09/02)
The activation of C-H bonds has revolutionized modern synthetic chemistry. However, no general strategy for enantiospecific C-H activation has been developed to date. We herein report an enantiospecific C-H activation reaction followed by deuterium incorporation at stereogenic centers. Mechanistic studies suggest that the selectivity for the α-position of the directing heteroatom results from a four-membered dimetallacycle as the key intermediate. This work paves the way to novel molecular chemistry on nanoparticles.