Tetrahedron Asymmetry p. 1947 - 1956 (1995)
Update date:2022-08-16
Topics:
Cardillo, Giuliana
Gentilucci, Luca
Tomasini, Claudia
Tomasoni, Laura
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.
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