17881-97-9Relevant academic research and scientific papers
Chemical Synthesis of [2H]-Ethyl Tosylate and Exploration of Its Crypto-optically Active Character Combining Complementary Spectroscopic Tools
Buisson, David-Alexandre,Crassous, Jeanne,Feuillastre, Sophie,Lesot, Philippe,Naret, Timothee,Pieters, Gregory,Polavarapu, Prasad L.,Puente, Andrew R.
supporting information, p. 8846 - 8849 (2020/12/02)
Small chiral molecules are excellent candidates to push the boundaries of enantiodiscrimination analytical techniques. Here is reported the synthesis of two new deuterated chiral probes, (R)- and (S)-[2H]-ethyl tosylate, obtained with high enantiomeric ex
Configurational stability of oxymethyllithiums as intermediates in intramolecular rearrangements
Kapeller, Dagmar C.,Brecker, Lothar,Hammerschmidt, Friedrich
, p. 9582 - 9588 (2008/12/20)
Several homochiral oxymethyllithiums, chiral by virtue of the hydrogen isotopes protium and deuterium, were prepared. They were tested for their microscopic configurational stability in intramolecular isomerizations, such as the silyl- and germyl-[1, 2]-r
Air-assisted addition of grignard reagents to olefins. A simple protocol for a three-component coupling process yielding alcohols
Nobe, Youhei,Arayama, Kyohei,Urabe, Hirokazu
, p. 18006 - 18007 (2007/10/03)
Silylmethyl, tertiary-alkyl, alkenyl, and aryl Grignard reagents underwent intermolecular addition to olefins, such as styrenes, conjugated dienes, and enynes under an air atmosphere to give homologated alcohols. For example, (trimethylsilyl)methylmagnesi
Direct chemical synthesis of chiral methanol of 98% ee and its conversion to [2H1,3H]methyl tosylate and [ 2H1,3H-methyl]methionine
Simov, Biljana Peric,Wuggenig, Frank,Mereiter, Kurt,Andres, Hendrik,France, Julien,Schnelli, Peter,Hammerschmidt, Friedrich
, p. 13934 - 13940 (2007/10/03)
This paper describes the synthesis of chiral methanols [(R)- and (S)-CHDTOH] in a total of 12 steps starting from (chloromethyl) dimethylphenylsilane. The metalated carbamates derived from (dimethylphenylsilyl)methanol and secondary amines were borylated at low temperatures (-78 or -94°C) using borates derived from fert-butyl alcohol and (+)-pinane-2,3-diol or (R,R)-1,2-dicyclohexylethane-1,2-diol to give diastereomeric boronates (dr 1:1 to 5:1). The carbamoyloxy group could be replaced smoothly with inversion of configuration by an isotope of hydrogen using LiAIH(D)4 [or LiBEt3H(D,T)]. If the individual diastereomeric boronates were reduced with LiAID4 and oxidized with H2O2/NaHCO3, monodeuterated (dimethylphenylsilyl)methanols of ee > 98% resulted. The absolute configurations of the boronates were based on a single-crystal X-ray structure analysis. Brook rearrangement of the enantiomers of (dimethylphenylsilyl)-[ 2H1,3H]methanol prepared similarly furnished the chiral methanols which were isolated as 3,5-dinitrobenzoates in 81% and 90% yield, respectively. For determination of the enantiomeric excesses (98%), the methyl groups were transferred to the nitrogen of (S)-2-methylpiperidine and 3H{1H} NMR spectra were recorded. The Brook rearrangement is a stereospecific process following a retentive course. The chiral methanols were also transformed into methyl tosylates used to prepare [2H 1,3H-methyl]methionines in high overall yields (>80%).
Use of (phenyldimethylsilyl)methoxymethyl and (phenyldimethylsilyl)methyl ethers as protecting groups for sugar hydroxyls
Boons,Elie,Van der Marel,Van Boom
, p. 2197 - 2200 (2007/10/02)
The reagent (phenyldimethylsilyl)methoxymethyl chloride (SMOM-Cl) proved to be very convenient for the formation of the corresponding SMOM ethers of primary and secondary hydroxyls of sugars. Further, (phenyldimethylsilyl)methanol (SMOH), the precursor of
