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.

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.
1995
Cardillo G.; Gentilucci L.; Tomasini C.; Tomasoni L.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/916673
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