(4S,5S)-4-benzylamino-5-[((terf-butyl)diphenylsilyl)oxymethyl]-dihydro- 2(3H)-furanone. A new intermediate for the enantiospecific synthesis of β-aminoesters and β-lactams

Article abstract of DOI:10.1016/0040-4039(95)01417-G

Conjugate addition of benzylamine to (S)-5-hydroxymethyl-2(5H)-furanone generated the new aminolactone (2b) as a single diastereomer. The C4/C5 trans relationship was confirmed by X-ray crystal structure determination of the corresponding t-butyldiphenylsilyl ether. Elaboration of aminolactone (2b) to β-aminoesters and β-lactams is also described.