The synthesis of chiral aminoalcohols 4 derived from (S)-tryptophan is described, by reaction of the protected amino acid 3 with various Grignard reagents. The aminoalcohols were transformed into the corresponding oxazolidin-2-ones 2 and acylated with 2-butenoyl chloride and 2-hexenoyl chloride, affording the imides 5a-e. The conformational analysis of both the oxazolidin-2-ones 2 and the Michael acceptors 5 was performed by means of 1H NMR, NOEDIF experiments and semiempirical AM1 calculations. © 1995.
Cardillo G., Gentilucci L., Tomasini C., Tomasoni L. (1995). Synthesis of new chiral auxiliaries derived from (S)-tryptophan. TETRAHEDRON-ASYMMETRY, 6(8), 1947-1955 [10.1016/0957-4166(95)00254-M].
Synthesis of new chiral auxiliaries derived from (S)-tryptophan
Gentilucci L.;Tomasini C.;Tomasoni L.
1995
Abstract
The synthesis of chiral aminoalcohols 4 derived from (S)-tryptophan is described, by reaction of the protected amino acid 3 with various Grignard reagents. The aminoalcohols were transformed into the corresponding oxazolidin-2-ones 2 and acylated with 2-butenoyl chloride and 2-hexenoyl chloride, affording the imides 5a-e. The conformational analysis of both the oxazolidin-2-ones 2 and the Michael acceptors 5 was performed by means of 1H NMR, NOEDIF experiments and semiempirical AM1 calculations. © 1995.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
