Highly diastereoselective hydroxyalkylation of phenols with chiral glyoxylates was performed. Hydrolysis or reduction of the esters 3 afforded 2-hydroxymandelic acids 6 and diols 5 in high yields and enantiomeric pure form. Mechanistic evidence of chelation-controlled reaction comes from the crystal structure determination of titanium phenoxide complex 8.

Stereoselective synthesis of optically active 2-hydroxymandelic acids and esters via Friedel - Crafts coordinated reaction: Crystal structure of chiral dichloro[2-(1-oxido-1-menthoxy-carbonylmethyl)-4-methoxyphenoxido- O,O,O]titanium / Bigi, F.; Bocelli, G.; Maggi, R.; Sartori, G.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 64:14(1999), pp. 5004-5009. [10.1021/jo982170o]

Stereoselective synthesis of optically active 2-hydroxymandelic acids and esters via Friedel - Crafts coordinated reaction: Crystal structure of chiral dichloro[2-(1-oxido-1-menthoxy-carbonylmethyl)-4-methoxyphenoxido- O,O,O]titanium

Bigi F.;Maggi R.;Sartori G.
1999-01-01

Abstract

Highly diastereoselective hydroxyalkylation of phenols with chiral glyoxylates was performed. Hydrolysis or reduction of the esters 3 afforded 2-hydroxymandelic acids 6 and diols 5 in high yields and enantiomeric pure form. Mechanistic evidence of chelation-controlled reaction comes from the crystal structure determination of titanium phenoxide complex 8.
1999
Stereoselective synthesis of optically active 2-hydroxymandelic acids and esters via Friedel - Crafts coordinated reaction: Crystal structure of chiral dichloro[2-(1-oxido-1-menthoxy-carbonylmethyl)-4-methoxyphenoxido- O,O,O]titanium / Bigi, F.; Bocelli, G.; Maggi, R.; Sartori, G.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 64:14(1999), pp. 5004-5009. [10.1021/jo982170o]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2887141
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