C. W. Jefford, F. D. V. D. Naide, K. Sienkiewicz
Apr 1, 1996
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0
Influential Citations
25
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Enantiomerically pure primary amines possessing an epimerizable center, such as α-amino acids and their ester hydrochlorides, undergo condensation with tetrahydro-2,5-dimethoxyfuran 2 in acetic acid or acetic acid containing sodium acetate at 80°C for 30 min. to give the corresponding 1-(1H-pyrrolyl) derivatives with partial racemization (9–18%). By replacing the solvent with a stirred mixture of aqueous acetic acid and 1,2-dichloroethane in the case of the acids and with water-1,2-dichloroethane for the ester hydrochlorides, repetition of the previous experiment gives the corresponding pyrroles in high yield and with complete retention of configuration. s-Aminoalcohols are also efficiently converted to their 1-(1H-pyrrolyl) derivatives in a stirred, warm mixture of aqueous acetic acid and 1,2-dichloroethane.