The alkylation of aromatic compounds, such as benzene, toluene, chlorobenzene, and naphthalene, with optically active (S)-alkyl 2-(sulfonyloxy)propionates and (R)-alkyl 3-(sulfonyloxy)butanoates in the presence of AlCl3 afforded optically active (S)-alkyl 2-arylpropionates and (S)-alkyl 3-arylbutanoates in fair to good chemical yields (40-84\%) and in good to excellent optical yields (61-97\%). As usually occurs in Friedel-Crafts alkylation reactions, poor regioselectivity was observed.

STEREOSPECIFIC FRIEDEL-CRAFTS ALKYLATION OF AROMATIC-COMPOUNDS - SYNTHESIS OF OPTICALLY-ACTIVE 2-ARYLALKANOIC AND 3-ARYLALKANOIC ESTERS / O. PICCOLO, U. AZZENA, G. MELLONI, G. DELOGU, E. VALOTI. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 56:1(1991), pp. 183-187.

STEREOSPECIFIC FRIEDEL-CRAFTS ALKYLATION OF AROMATIC-COMPOUNDS - SYNTHESIS OF OPTICALLY-ACTIVE 2-ARYLALKANOIC AND 3-ARYLALKANOIC ESTERS

E. VALOTI
Ultimo
1991

Abstract

The alkylation of aromatic compounds, such as benzene, toluene, chlorobenzene, and naphthalene, with optically active (S)-alkyl 2-(sulfonyloxy)propionates and (R)-alkyl 3-(sulfonyloxy)butanoates in the presence of AlCl3 afforded optically active (S)-alkyl 2-arylpropionates and (S)-alkyl 3-arylbutanoates in fair to good chemical yields (40-84\%) and in good to excellent optical yields (61-97\%). As usually occurs in Friedel-Crafts alkylation reactions, poor regioselectivity was observed.
stereospecific Friedel-crafts ; alkilation ; aromatic compounds ; optically active arylalkanoic derivatives
Settore CHIM/08 - Chimica Farmaceutica
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/183006
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