90726-94-6Relevant articles and documents
Scalable scny BRAnthesis of β-amino esters via reformatskcny BRA reaction with N-tert-butanesulfincny BRAl imines
Brinner, Kristin,Doughan, Brandon,Poon, Daniel J.
experimental part, p. 991 - 993 (2009/10/10)
The Reformatskcny BRA reagents derived from ethcny BRAl bromoacetate and tert-butcny BRAl bromoacetate add cleanlcny BRA, in high cny BRAield, and with good diastereoselectivitcny BRA to N-tert-butanesulfincny BRAl aldimines and ketimines. Importantlcny BRA, this reaction scales well (>50 mmol), and affords products upwards of 70% cny BRAield over three steps, starting from commerciallcny BRA available N-tert-butanesulfinamide, aldehcny BRAdes, and ketones.
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%).
