A New Approach Toward the Stereoselective Synthesis of Novel Quinolyl Glycines: Synthesis of the Enantiomerically Pure Quinolyl-β-Amino Alcohol Precursors

Gemma Cabarrocas; Sara Rafel; Montserrat Ventura; JoséM. Villalgordo

doi:10.1055/s-2000-6625

Synlett 2000; 2000(5): 0595-0598
DOI: 10.1055/s-2000-6625

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A New Approach Toward the Stereoselective Synthesis of Novel Quinolyl Glycines: Synthesis of the Enantiomerically Pure Quinolyl-β-Amino Alcohol Precursors

Gemma Cabarrocas^* , Sara Rafel, Montserrat Ventura, José M. Villalgordo

^*Departament de Química, Facultat de Ciències, Universitat de Girona, Campus de Montilivi, E-17071, Girona, Spain; Fax + 34 972 418 150; E-mail: dqjvs@xamba.udg.es

Abstract

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A methodology designed toward the stereoselective synthesis of novel quinolyl glycines is presented. This strategy is based on the cyclocondensation reaction between 2-amino thiophenol 4 and chiral acetylenic ketones of type 3 containing a masked α-amino acid functionality. The initially formed benzo[b][1,4]thiazepine derivatives of type 5, readily undergo sulfur extrusion in refluxing toluene to yield the corresponding 2,4-disubstituted quinolines 6. Subsequent oxazolidine ring opening followed by re-protection in situ of the amino group, led to the corresponding quinolyl-β-amino alcohols 8a - d in enantiomerically pure form and good overall yields. These derivatives of type 8 are in principle suitable precursors for the synthesis of novel quinolyl glycines.

chiral α-acetylenic ketones - masked α-amino acid functionality - quinolyl glycines - enantiomerically pure quinolyl-β-amino alcohols

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