Volume 22, Issue 16
Preparative Organic Chemistry
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ChemInform Abstract: Highly Regio- and Diastereoselective Friedel-Crafts Alkylation of Phenols. Synthesis of 2-Hydroxymandelic Esters.

F. BIGI

F. BIGI

Ist. Chim. Org., Univ., I-43100 Parma, Italy

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G. CASNATI

G. CASNATI

Ist. Chim. Org., Univ., I-43100 Parma, Italy

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G. SARTORI

G. SARTORI

Ist. Chim. Org., Univ., I-43100 Parma, Italy

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C. DALPRATO

C. DALPRATO

Ist. Chim. Org., Univ., I-43100 Parma, Italy

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R. BORTOLINI

R. BORTOLINI

Ist. Chim. Org., Univ., I-43100 Parma, Italy

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First published: April 23, 1991

Abstract

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ChemInform Abstract

The use of mandelic acid as a drug and the interest in asym. electrophilic aromatic substitution results in the synthesis of the title esters (III), (IV), (VI) and (VII). The diastereomeric ratio depends on the bulkiness of the chiral esters (II) and (V) and on the Lewis acid used. Best results are achieved with TiCl4.

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