155550-71-3Relevant academic research and scientific papers
Synthetic method of resolving agent hydrogen isopropylidene glycerol phthalate
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Paragraph 0023; 0024; 0025, (2017/01/02)
The invention relates to a resolving agent hydrogen isopropylidene glycerol phthalate. In the method, (S)-(-)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane or (R)-(+)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane is employed as a raw material and is reacted with hydrogen potassium phthalate to generate S/R-hydrogen isopropylidene glycerol phthalate. Compared with the prior art, the resolving agent is prepared directly from a commercial chiral raw material to directly synthesize the resolving agent hydrogen isopropylidene glycerol phthalate in a one-step manner. The raw materials are easy to obtain and are low in cost.
Peptide-catalyzed stereoselective conjugate addition reactions generating all-carbon quaternary stereogenic Centers
Kastl, Robert,Wennemers, Helma
supporting information, p. 7228 - 7232 (2013/07/26)
A powerful catalyst: Quaternary stereogenic centers adjacent to tertiary stereocenters were formed with high diastereoselectivities and enantioselectivities in conjugate addition reactions between aldehydes and β,β-disubstituted nitroolefins by using a peptidic catalyst (see scheme). γ-Amino acids and heterocyclic compounds bearing quaternary stereogenic centers are easily accessible from the products. Copyright
Isopropylidene glycerol hydrogen phthalate: A new resolving agent application to the resolution of 1-arylethylamines
Pallavicini, Marco,Valoti, Ermanno,Villa, Luigi,Piccolo, Oreste
, p. 1117 - 1122 (2007/10/03)
Hydrogen phthalates of (R)- and (S)-isopropylidene glycerol, obtainable from racemic isopropylidene glycerol by reaction with phthalic anhydride and successive resolution with (S)- and (R)-1-phenylethylamine or, alternatively, from (R)- and (S)-isopropylidene glycerol, were regarded as potential new resolving agents A range of important 1-arylethylamines was selected to test their resolving capability. In particular, trial resolutions were carried out using equivalent amounts of racemic amine and hydrogen phthalate of (R)-isopropylidene glycerol The salts of the S isomers selectively crystallized from methanol or 2-propanol allowing to recover the (S)-1-arylethylamines in high chemical and optical yields. Copyright
Synthesis of (R)- and (S)-isopropylidene glycerol
Pallavicini,Valoti,Villa,Piccolo
, p. 5 - 8 (2007/10/02)
The preparation of (R)- and (S)-isopropylidene glycerol 1 of high enantiomeric excess (> 98%) was accomplished through salt formation between their hydrogen phthalates with (S)- and (R)-1-methylbenzylamine [MBA] respectively, selective crystallization of these salts and subsequent regeneration of optically active compounds 1 by saponification. The progress of resolution was followed by HPLC analysis on Chiralcel OJ, after converting the hydrogen phthalates into the corresponding mono methyl esters by diazomethane.
