140170-64-5Relevant academic research and scientific papers
STEREOSELECTIVE SYNTHESIS OF OPTICALLY ACTIVE DIETHANOLOAMINES UTILIZING DIASTEREOSELECTIVE REACTION OF 1,3-OXAZOLIDINES WITH GRIGNARD REAGENTS
Higashiyama, Kimio,Nakagawa, Katuyuki,Takahashi, Hiroshi
, p. 2007 - 2018 (2007/10/03)
The highly diastereoselective addition of isopropoxydimethylsilylmethylmagnesium chloride to N-benzyl-1,3-oxazolidines derived from (R)-phenylglycinol, followed by oxidation of adducts with hydrogen peroxide in the presence of potassium fluoride, provided the 1-substituted (1R, 1'R)-N-benzyl-1'-phenyl-2,2'-dihydroxydiethylamines (1a-d).
Stereoselective ring opening of chiral oxazolidines by reformatsky reagents: An enantioselective entry to β-amino esters
Andres, Celia,Gonzalez, Alfonso,Pedrosa, Rafael,Perez-Encabo, Alfonso
, p. 2895 - 2898 (2007/10/02)
Chiral oxazolidines obtained by condensation of aldehydes with (-).(R)- or (+).(S)-N-benzylphenylglycinol react with the Reformatsky reagent derived from ethyl bromoacetate, in mild reaction conditions (Et2O or CH2Cl2, 0°C, 15-60 min), leading to ethyl β-amino carboxylates in moderate to good diastereomeric excess (60-92%). These ring opening products are transformed into primary β-aminoesters, in one step, by debenzylation with H2/Pd on carbon without loss of their stereochemical integrity. In this way, ethyl β-amino carboxylates can be obtained in both enantiomeric forms, with chemical yields ranging 55-76% and moderate to good e.e. (60-92%).
