Enantiopure 4-amino-3-hydroxymethyl-1,2,3,4-tetrahydroquinolines are synthesized by using an intramolecular cycloaddition of chiral nitrones prepared from aldehydes 5 and (R)-α-(hydroxymethyl)benzylhydroxylamine. Reaction times of the nitrone cycloaddition were optimized by activation under MW-assisted conditions. The absolute configuration of the products was determined by X-ray analysis.
Synthesis of enantiopure 4-amino-3-hydroxymethyl-tetrahydroquinolines via an intramolecular nitrone cycloaddition / G. Broggini, F. Colombo, I. De Marchi, S. Galli, M. Martinelli, G. Zecchi. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 18:12(2007 Jul 04), pp. 1495-1501. [10.1016/j.tetasy.2007.06.004]
Synthesis of enantiopure 4-amino-3-hydroxymethyl-tetrahydroquinolines via an intramolecular nitrone cycloaddition
F. ColomboSecondo
;M. MartinelliPenultimo
;
2007
Abstract
Enantiopure 4-amino-3-hydroxymethyl-1,2,3,4-tetrahydroquinolines are synthesized by using an intramolecular cycloaddition of chiral nitrones prepared from aldehydes 5 and (R)-α-(hydroxymethyl)benzylhydroxylamine. Reaction times of the nitrone cycloaddition were optimized by activation under MW-assisted conditions. The absolute configuration of the products was determined by X-ray analysis.
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